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 722747Notes

Reaction equation

HRID 722747 reaction equation
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]

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bbb63866c9ba4920964a4f6ca35ec132
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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