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Sodium Bicarbonate → (2S)-2-[[N-(2-methoxybenzyl)-N-(2-oxo-3,3-diphenylpropyl)amino)methyl]piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester

HRID 1006352
Notes
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Reaction equation

HRID 1006352 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:10][C@@H:9]1[CH:24]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][O:27][C:28]1[CH:51]=[CH:50][CH:49]=[CH:48][C:29]=1[CH2:30][NH:31][CH2:32][C:33](=[O:47])[CH:34]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[Na].C(=O)([O-])O.[Na+]>ClCCl.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:10][C@@H:9]1[CH2:24][N:31]([CH2:30][C:29]1[CH:48]=[CH:49][CH:50]=[CH:51][C:28]=1[O:27][CH3:26])[CH2:32][C:33](=[O:47])[CH:34]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 226745333-(2-Methoxybenzylamino)-1,1-diphenylpropan-2-oneHCID 865896504-Benzyl 1-(tert-butyl) (R)-2-formylpiperazine-1,4-dicarboxylate

Product 1

HCID 69744922(2S)-2-[[N-(2-methoxybenzyl)-N-(2-oxo-3,3-diphenylpropyl)amino)methyl]piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester
Yield 63.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, to a solution of (2R)-2-formylpiperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (2.64 g) and 3-(2-methoxybenzylamino)-1,1-diphenylpropan-2-one (3.66 g) in dichloromethane (30 ml) was added acetic acid (0.607 ml) and sodium tritacetoxyborohydride (4.82 g) under ice-cooling, and then it was stirred at room temperature for 3 hours. The reaction mixture was poured into aqueous sodium hydrogen carbonate (100 ml) and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (82 g) using a mixed solvent of hexane and ethyl acetate (3:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give (2S)-2-[[N-(2-methoxybenzyl)-N-(2-oxo-3,3-diphenylpropyl)amino]methyl]piperazine-1,4-dicarboxylic acid 4-benzyl ester 1-tert-butyl ester (3.24 g) as a syrup.

Workup

  1. temperaturecooling
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel (82 g)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0a91a733e9cc4d2baef2e97f7b07c36b
Source dataset
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06787543B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes