반응 #2260184

ord-73764a30e3d54f06995283e71f7d2f4c

반응 방정식

CC(=O)O
acetic acid
Cn1ncnc1S[C@H]1[C@H]2[C@H](C(=O)OC(C)(C)C)[C@H]2[C@](NC(=O)OC(C)(C)C)(C(=O)OC(C)(C)C)[C@@H]1OCc1ccc(Cl)c(Cl)c1
di-tert-butyl (1R,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]-4-[(2-methyl-1,2,4-triazol-3-yl)sulfanyl]bicyclo[3.1.0]hexane-2,6-dicarboxylate
→
Cl.Cn1ncnc1S[C@H]1[C@H]2[C@H](C(=O)O)[C@H]2[C@](N)(C(=O)O)[C@@H]1OCc1ccc(Cl)c(Cl)c1
title compound
Cl.Cn1ncnc1S[C@H]1[C@H]2[C@H](C(=O)O)[C@H]2[C@](N)(C(=O)O)[C@@H]1OCc1ccc(Cl)c(Cl)c1
(1R,2R,3S,4S,5R,6R)-2-amino-3-[(3,4-dichlorobenzyl)oxy]-4-[(1-methyl-1H-1,2,4-triazol-5-yl)sulfanyl]bicyclo[3.1.0]hexane-2,6-dicarboxylic acid hydrochloride

반응물

CC(=O)O
acetic acid
Cn1ncnc1S[C@H]1[C@H]2[C@H](C(=O)OC(C)(C)C)[C@H]2[C@](NC(=O)OC(C)(C)C)(C(=O)OC(C)(C)C)[C@@H]1OCc1ccc(Cl)c(Cl)c1
di-tert-butyl (1R,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]-4-[(2-methyl-1,2,4-triazol-3-yl)sulfanyl]bicyclo[3.1.0]hexane-2,6-dicarboxylate

시약

없음

용매

O
water

반응 조건

온도
140°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타seal
  2. 2
    온도Cool
  3. 3
    농축concentrate the mixture to dryness
  4. 4
    workup.ADDITIONadd 5 N hydrochloric acid (2 mL), acetonitrile (2 mL), and transfer to a vial

실험 절차

Add acetic acid (2.0 mL) and water (2.0 mL) to di-tert-butyl (1R,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-3-[(3,4-dichlorophenyl)methoxy]-4-[(2-methyl-1,2,4-triazol-3-yl)sulfanyl]bicyclo[3.1.0]hexane-2,6-dicarboxylate (0.305 g, 0.445 mmol) in a microwave vessel and seal and heat the mixture to 140° C. for 25 minutes. Cool and concentrate the mixture to dryness, and then add 5 N hydrochloric acid (2 mL), acetonitrile (2 mL), and transfer to a vial. Lyophilize overnight to yield the title compound as a white solid (0.227 g, 0.445 mmol; 95%): MS (m/z): 473/475/477 (M+1).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US09056844B2uspto-grants-2015_06