(1R,4S,5S)-5-((3-Hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol
Round 1
Reviewer 1 Report
This is a good short paper that can be accepted with only a few minor corrections:
lines 50 and 76 - change 'originate' to 'produce'
lines 79-83 we do not have proper sentences. Line 79 change '3c. The singlet....' to '3c: a singlet....' and line 82 change 'tetrazole ring. The.....' to 'tetrazole ring: a.....'.
line 85, change 'since has a' to 'since it has a'
References - these need to be changed to all use the standard abbreviations for journals (CASSI) rather than the full names, so for example: Chem. Soc. Rev.; Tetrahedron Lett.; Eur. J. Org. Chem.; J. Am. Chem. Soc.; Curr. Med. Chem.; J. Org. Chem.; Org. Process Res. Dev.; Helv. Chim. Acta.
Author Response
Reviewer #1 Overall Comment:
This is a good short paper that can be accepted with only a few minor corrections:
Authors answer: Thank you for your evaluation.
Reviewer #1 Specific Comments: lines 50 and 76 - change 'originate' to 'produce'
Authors answer and/or action taken: We corrected the 'originate' to 'produce'
Reviewer #1 Specific Comments: lines 79-83 we do not have proper sentences. Line 79 change '3c. The singlet....' to '3c: a singlet....' and line 82 change 'tetrazole ring. The.....' to 'tetrazole ring: a.....'.
Authors answer and/or action taken: We corrected in line 79 the '3c. The singlet....' to '3c: a singlet....' and in line 82 the 'tetrazole ring. The.....' to 'tetrazole ring: a.....'.
Reviewer #1 Specific Comments: line 85, change 'since has a' to 'since it has a'
Authors answer and/or action taken: We corrected in line 85, the 'since has a' to 'since it has a'
Reviewer #1 Specific Comments: References - these need to be changed to all use the standard abbreviations for journals (CASSI) rather than the full names, so for example: Chem. Soc. Rev.; Tetrahedron Lett.; Eur. J. Org. Chem.; J. Am. Chem. Soc.; Curr. Med. Chem.; J. Org. Chem.; Org. Process Res. Dev.; Helv. Chim. Acta.
Authors answer and/or action taken: We corrected the references with the abbreviations for journals (CASSI), example “Chem. Soc. Rev. 2002,….”
Reviewer 2 Report
The Authors report a novel and effective synthesis for the target compound (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol. The molecule has been characterized in solution by mean of 1H, 13C, HSQC, and MS. The structural elucidation fits with the structure proposed and it is in agreement with similar compounds previously reported. The paper is well structured and the English level is fine.
In order to increase the quality of the discussion, I suggest to extend the 1H NMR description by adding a couple of shapshots of protons 1-9 and by discussing the observed multiplicity.
Author Response
Reviewer #2 Overall Comment:
“The Authors report a novel and effective synthesis for the target compound (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol. The molecule has been characterized in solution by mean of 1H, 13C, HSQC, and MS. The structural elucidation fits with the structure proposed and it is in agreement with similar compounds previously reported. The paper is well structured and the English level is fine.
In order to increase the quality of the discussion, I suggest to extend the 1H NMR description by adding a couple of shapshots of protons 1-9 and by discussing the observed multiplicity.”
Authors answer and/or action taken: We thanks the reviewer for the evaluation and for the specific comment.We added at the SI the snapshots of protons 1-9 and also included in the main manuscript the discussion of the multiplicity, “ a singlet at 3.96 ppm, corresponding to the methyl group linked to the tetrazole ring, and multiplets corresponding to the geminal protons of the thioether a 4.30 - 4.29 ppm, the alcohol a 4.59 – 4,58 ppm and the amine a 3.29 – 3.26 ppm. The signals for the hydroxypropyl chain can be observed as a quartet (J = 6.9 Hz, 2.77 ppm), a multiplet (1.76-1.67 ppm), and a triplet (J = 6.4 Hz, 3.60 ppm), corresponding to the protons vicinal to the amine, to the middle-chain methylene, and to the protons geminal to the hydroxyl group, respectively”
We also improved the proton attribution regarding the multiplicity in “ 4.59 – 4,58 (m, 1H), 4.30 - 4.29 (m, 1H), 3.96 (s, 3H), 3.60 (t, J = 6.4 Hz, 2H), 3.29 – 3.26 (m, 1H), 2.77 (q, J = 6.9 Hz, 2H), 1.76-1.67 (m, 2H).”
