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Water → 4-(tert-butyl-dimethyl-silanyloxy)-3-({7-[(naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carbonyl}-amino)-butyric Acid

HRID 722747
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HRID 722747 반응식
C([O:8][C:9](=[O:50])[CH2:10][CH:11]([NH:21][C:22]([CH:24]1[N:29]2[C:30](=[O:49])[CH:31]([NH:36][C:37]([C:39]3[CH:48]=[CH:47][C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH:40]=3)=[O:38])[CH2:32][CH:33]=[CH:34][CH2:35][CH:28]2[CH2:27][CH2:26][CH2:25]1)=[O:23])[CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])C1C=CC=CC=1.O>CO.[OH-].[Na+]>[C:17]([Si:14]([CH3:16])([CH3:15])[O:13][CH2:12][CH:11]([NH:21][C:22]([CH:24]1[N:29]2[C:30](=[O:49])[CH:31]([NH:36][C:37]([C:39]3[CH:48]=[CH:47][C:46]4[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=4)[CH:40]=3)=[O:38])[CH2:32][CH:33]=[CH:34][CH2:35][CH:28]2[CH2:27][CH2:26][CH2:25]1)=[O:23])[CH2:10][C:9]([OH:50])=[O:8])([CH3:19])([CH3:18])[CH3:20]
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참가 물질

5

반응물 2

HCID 962WaterHCID 696596654-(tert-Butyl-dimethyl-silanyloxy)-3-({7-[(naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carbonyl}-amino)-butyric Acid Benzyl Ester

생성물 1

HCID 696601414-(tert-butyl-dimethyl-silanyloxy)-3-({7-[(naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carbonyl}-amino)-butyric Acid

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 14798Sodium Hydroxide용매2회

실험 절차

4-(tert-Butyl-dimethyl-silanyloxy)-3-({7-[(naphthalene-2-carbonyl)-amino]-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carbonyl}-amino)-butyric acid benzyl ester, 114, (0.52 gm) is dissolved in 10 mL methanol, to which 1.73 mL of 1N aqueous sodium hydroxide is added at RT. The reaction is stirred for 5 h and a second aliquot (0.7 mL) of 1N sodium hydroxide solution is added. The reaction is allowed to proceed for 18 h at RT. Water is added and the mixture is extracted three times with diethyl ether. The aqueous layer is then acidified to pH ˜3 with 10% aqueous citric acid, and extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium chloride, dried over sodium sulfate powder, and concentrated in vauo to afford the desired product.

후처리

  1. additionis added at RT
  2. waitto proceed for 18 h at RT
  3. extractionthe mixture is extracted three times with diethyl ether
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate powder
  7. concentrationconcentrated in vauo

출처 및 근거

ORD 기록
ord-bbb63866c9ba4920964a4f6ca35ec132
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07138395B2

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