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Acetic Acid → HCID 69215857, compound

HRID 269467
Notes
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Reaction equation

HRID 269467 reaction equation
C(O[BH-]([O:10][C:11](=[O:13])[CH3:12])OC(=O)C)(=O)C.C[N+:15]([CH3:18])(C)C.C(OC(=O)CN[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)C.C(=O)[CH2:34][CH3:35].[C:37](O)(=O)[CH3:38]>C(Cl)Cl>[CH2:25]([CH2:37][CH2:38][CH2:18][NH:15][CH2:12][C:11]([O:10][CH2:34][CH3:35])=[O:13])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 80908N-Benzylglycine ethyl esterHCID 13696215Tetramethylammonium Triacetoxyborohydride (>90%)

Product 1

HCID 69215857HCID 69215857, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Tetramethylammonium triacetoxyborohydride was added to a solution of N-benzylglycine ethyl ester (1.87 mL, 10 mmol), propionaldehyde (1.05 mL, 14 mmol) and acetic acid (0.6 mL) in CH2Cl2 (20 mL), and the resulting mixture was stirred at room temperature for 18 h. The reaction mixture was partitioned between aqueous Na2CO3 (2 M, 100 mL) and CH2Cl2 (3×20 mL) and the combined organic layers were dried over Na2SO4 and concentrated in vacuo to give ethyl 2-[benzylpropylamino]acetate as a yellow oil (2.25 g, 96% yield). LCMS (method B): 1.52 min, 236.0 (M+H)+.

Workup

  1. customThe reaction mixture was partitioned between aqueous Na2CO3 (2 M, 100 mL) and CH2Cl2 (3×20 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c4d2a325be84e38a11220e5ac5c7618
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07446204B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes