반응 #48706

ord-3f30fb1c0fa74e61bd19f8a701e01af4

반응 방정식

CC(=O)N[C@@H](Cc1cccc(OCc2ccccc2)c1)[C@H](O)[C@H]1CO[C@@H](OCC2(C)CCCC2)CN1C(=O)OC(C)(C)C
(2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-benzyloxyphenyl)-1-hydroxypropyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester
[H][H]
hydrogen
→
CC(=O)N[C@@H](Cc1cccc(O)c1)[C@H](O)[C@H]1CO[C@@H](OCC2(C)CCCC2)CN1C(=O)OC(C)(C)C
desired compound
수율 98.5%
CC(=O)N[C@@H](Cc1cccc(O)c1)[C@H](O)[C@H]1CO[C@@H](OCC2(C)CCCC2)CN1C(=O)OC(C)(C)C
(2R,5R)-5-[(1S,2S)-2-Acetylamino-1-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester
수율 98.5%

반응물

CC(=O)N[C@@H](Cc1cccc(OCc2ccccc2)c1)[C@H](O)[C@H]1CO[C@@H](OCC2(C)CCCC2)CN1C(=O)OC(C)(C)C
(2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-benzyloxyphenyl)-1-hydroxypropyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester
[H][H]
hydrogen

시약

[OH-].[OH-].[Pd+2]
palladium hydroxide on carbon

용매

CO
methanol

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    여과Filter
  2. 2
    농축concentrate

실험 절차

Hydrogenate (2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-benzyloxyphenyl)-1-hydroxypropyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester (244 mg) in methanol (15 mL) with 20% palladium hydroxide on carbon (26 mg) at 50 psi hydrogen for 18 hours. Filter and concentrate to give the desired compound (204 mg). MS(ES): m/z=507 [M+H]

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07745438B2uspto-grants-2010_06