Lithium Hydroxide → N-[(S)-5-(2-Benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-2,2-dimethyl-malonamic acid

HRID 30999Notes

Reaction equation

HRID 30999 reaction equation
C([O:3][C:4](=[O:37])[C:5]([CH3:36])([CH3:35])[C:6]([NH:8][C@@H:9]1[C:15](=[O:16])[N:14]([CH2:17][CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:13]2[CH:27]=[CH:28][CH:29]=[CH:30][C:12]=2[C:11]2[CH:31]=[CH:32][CH:33]=[CH:34][C:10]1=2)=[O:7])C.[OH-].[Li+]>C1COCC1.O.C(=O)([O-])[O-].[Na+].[Na+]>[CH2:20]([O:19][CH2:18][CH2:17][N:14]1[C:15](=[O:16])[C@@H:9]([NH:8][C:6](=[O:7])[C:5]([CH3:36])([CH3:35])[C:4]([OH:37])=[O:3])[C:10]2[CH:34]=[CH:33][CH:32]=[CH:31][C:11]=2[C:12]2[CH:30]=[CH:29][CH:28]=[CH:27][C:13]1=2)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 58972525N-[(S)-5-(2-Benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-2,2-dimethyl-malonamic acid ethyl ester

Product 1

HCID 58972495N-[(S)-5-(2-Benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-2,2-dimethyl-malonamic acidYield 94.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

N—[(S)-5-(2-Benzyloxy-ethyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl]-2,2-dimethyl-malonamic acid ethyl ester (127 mg, 0.25 mmol) were dissolved in THF (4.5 ml) and water (1.1 ml), treated with lithium hydroxide (25 mg, 1 mmol) and stirred for 18 h at ambient temperature. The mixture is diluted with aqueous saturated sodium carbonate and extracted twice with ethyl acetate. The aqueous phase is acidified with concentrated aqueous hydrogen chloride to pH 0 and extracted twice with ethyl acetate. The acidic organic layers were combined, dried over magnesium sulfate and evaporated to afford 112 mg (93%) of white foam. MS: m/e=472(M−H+).

Workup

  1. extractionextracted twice with ethyl acetate
  2. extractionextracted twice with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-64161f01c23448bc8468eaa49ce72159
Source dataset
uspto-grants-2008_09
Patent number
US07425551B2

Reaction notes

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