반응 #557100

ord-faa96a9288304ac99b67d5500bc58010

반응 방정식

Cc1ccc(SC[C@@H]2[C@@H](O)[C@H]3[C@H](C(=O)OC(C)(C)C)[C@H]3[C@]2(NC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1
Di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-3-(p-tolylsulfanylmethyl)bicyclo[3.1.0]hexane-2,6-dicarboxylate
O
water
CC(=O)O
acetic acid
→
Cc1ccc(SC[C@@H]2[C@@H](O)[C@H]3[C@H](C(=O)O)[C@H]3[C@]2(N)C(=O)O)cc1
title compound
수율 89.6%
Cc1ccc(SC[C@@H]2[C@@H](O)[C@H]3[C@H](C(=O)O)[C@H]3[C@]2(N)C(=O)O)cc1
(1S,2R,3S,4S,5R,6R)-2-Amino-4-hydroxy-3-{[(4-methylphenyl)sulfanyl]methyl}bicyclo[3.1.0]hexane-2,6-dicarboxylic acid
수율 89.6%

반응물

Cc1ccc(SC[C@@H]2[C@@H](O)[C@H]3[C@H](C(=O)OC(C)(C)C)[C@H]3[C@]2(NC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)cc1
Di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-3-(p-tolylsulfanylmethyl)bicyclo[3.1.0]hexane-2,6-dicarboxylate
O
water
CC(=O)O
acetic acid

시약

없음

반응 조건

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

후처리

  1. 1
    기타The solvent is removed under reduced pressure

실험 절차

Di-tert-butyl (1S,2R,3S,4S,5R,6R)-2-(tert-butoxycarbonylamino)-4-hydroxy-3-(p-tolylsulfanylmethyl)bicyclo[3.1.0]hexane-2,6-dicarboxylate (300 mg, 545.73 μmol) is placed in a microwave vial. To the vial is added water (2 mL, 110 mmol), and acetic acid (2 mL, 34.9 mmol). The mixture is heated in the microwave to 140° C. for 20 minutes. The solvent is removed under reduced pressure to give the title compound (165 mg, 489.04 μmol, 89.6%). MS (m/z): 338.0 (M+H).

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08629169B2uspto-grants-2014_01