Citric Acid → 4-(tert-Butyl-dimethyl-silanyloxy)-3-({6-[(naphthalene-2-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carbonyl}-amino)-butyric acid

HRID 1824443Notes

Reaction equation

HRID 1824443 reaction equation
C([O:8][C:9](=[O:49])[CH2:10][CH:11]([NH:21][C:22]([CH:24]1[N:28]2[C:29](=[O:48])[CH:30]([NH:35][C:36]([C:38]3[CH:47]=[CH:46][C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH:39]=3)=[O:37])[CH2:31][CH:32]=[CH:33][CH2:34][CH:27]2[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.[OH-].[Na+].O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:17]([Si:14]([CH3:16])([CH3:15])[O:13][CH2:12][CH:11]([NH:21][C:22]([CH:24]1[N:28]2[C:29](=[O:48])[CH:30]([NH:35][C:36]([C:38]3[CH:47]=[CH:46][C:45]4[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH:39]=3)=[O:37])[CH2:31][CH:32]=[CH:33][CH2:34][CH:27]2[CH2:26][CH2:25]1)=[O:23])[CH2:10][C:9]([OH:49])=[O:8])([CH3:19])([CH3:18])[CH3:20]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 695844714-(tert-Butyl-dimethyl-silanyloxy)-3-({6-[(naphthalene-2-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carbonyl}-amino)-butyric acid benzyl ester

Product 1

HCID 695844784-(tert-Butyl-dimethyl-silanyloxy)-3-({6-[(naphthalene-2-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carbonyl}-amino)-butyric acidYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution containing 4-(tert-Butyl-dimethyl-silanyloxy)-3-({6-[(naphthalene-2-carbonyl)-amino]-5-oxo-1,2,3,5,6,7,10,10a-octahydro-pyrrolo[1,2-a]azocine-3-carbonyl}-amino)-butyric acid benzyl ester (590 mg, 0.86 mmol) in MeOH (10 mL) is treated with 1N NaOH (2.5 mL) and stirred at rt for 12 hrs. The solution was poured into water, acidified to pH=3 with 10% citric acid, and extracted with EtOAc. The combined organic extracts are washed with brine and dried over Na2SO4. The solution is filtered and concentrated to yield 492 mg of desired product that was used without further purification. MS (ESI) 594 (M+1).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationThe solution is filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5d0b422ed0cc44b394ac1a6d0a480269
Source dataset
uspto-grants-2006_05
Patent number
US07041696B2

Reaction notes

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