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Trifluoroacetic acid → (2-Oxo-2,3,4,5-tetrahydro-benzo[e][1,4]diazepin-1-yl)-acetic acid ethyl ester

HRID 1253883
Notes
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Reaction equation

HRID 1253883 reaction equation
C(OC([N:8]1[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=2[N:11]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:10](=[O:25])[CH2:9]1)=O)(C)(C)C.[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29]>C(Cl)Cl>[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[CH2:23]([O:22][C:20](=[O:21])[CH2:19][N:11]1[C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[CH2:14][NH:8][CH2:9][C:10]1=[O:25])[CH3:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 686381191-Ethoxycarbonylmethyl-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert-butyl ester

Product 2

HCID 6422Trifluoroacetic acidHCID 68637366(2-Oxo-2,3,4,5-tetrahydro-benzo[e][1,4]diazepin-1-yl)-acetic acid ethyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a solution of 1-ethoxycarbonylmethyl-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert-butyl ester (125 mg, 0.36 mmol) in dry DCM (5 mL) was added trifluoroacetic acid (1.08 mL, 3 mL/mmol). The reaction mixture was stirred at r.t. for one hour. After completion of the reaction, as confirmed by TLC, excess of trifluoroacetic acid and DCM were evaporated in vacuo to afford trifluoroacetic acid salt of (2-oxo-2,3,4,5-tetrahydro-benzo[e][1,4]diazepin-1-yl)-acetic acid ethyl ester (119 mg, 92%) as a gummy solid which was used as such without any further purification for the next step.

Workup

  1. customAfter completion of the reaction
  2. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-c76f3e050f3a4f9386525b1d067cab76
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08455479B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes