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(2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-benzyloxyphenyl)-1-hydroxypropyl]-2-(1-methyl-cyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester → (2R,5R)-5-[(1S,2S)-2-Acetylamino-1-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester

HRID 20428
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HRID 20428 반응식
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:35])[C@@H:15]([NH:31][C:32](=[O:34])[CH3:33])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23]CC3C=CC=CC=3)[CH:18]=2)[CH2:12][O:11][C@@H:10]([O:36][CH2:37][C:38]2([CH3:43])[CH2:42][CH2:41][CH2:40][CH2:39]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([C@@H:14]([OH:35])[C@@H:15]([NH:31][C:32](=[O:34])[CH3:33])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([OH:23])[CH:18]=2)[CH2:12][O:11][C@@H:10]([O:36][CH2:37][C:38]2([CH3:43])[CH2:39][CH2:40][CH2:41][CH2:42]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
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참가 물질

5

반응물 2

HCID 68561840(2R,5R)-5-[(1S,2S)-2-Acetylamino-3-(3-benzyloxyphenyl)-1-hydroxypropyl]-2-(1-methyl-cyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 68562669(2R,5R)-5-[(1S,2S)-2-Acetylamino-1-hydroxy-3-(3-hydroxyphenyl)-propyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester수율 98.5%

시약·촉매·용매 2

HCID 9942167
Palladium hydroxide
촉매
HCID 887Methanol용매

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]

후처리

  1. filtrationFilter
  2. concentrationconcentrate

출처 및 근거

ORD 기록
ord-3f30fb1c0fa74e61bd19f8a701e01af4
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07745438B2

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