Trifluoroacetic acid → 1-methyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-one

HRID 1253879Notes

Reaction equation

HRID 1253879 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]([CH3:19])[C:10](=[O:20])[CH2:9]1)=O)(C)(C)C.[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24]>C(Cl)Cl>[F:21][C:22]([F:27])([F:26])[C:23]([OH:25])=[O:24].[CH3:19][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:20]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68638936tert-Butyl 1-methyl-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate

Product 2

HCID 6422Trifluoroacetic acidHCID 187582601-methyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepin-2-oneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-methyl-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid tert-butyl ester (70 mg, 0.25 mmol) in dry DCM (10 mL), was added trifluoroacetic acid (0.75 mL, 3 mL/mmol). The mixture was stirred at r.t. for 1 h. After the completion of the reaction as confirmed by TLC, excess of TFA and DCM were evaporated in vacuo to afford trifluoroacetic acid salt of 1-methyl-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-one (70 mg, 95%) as a gummy solid which was used as such for next coupling.

Workup

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

Sources & evidence

ORD record
ord-3246b5ae1c0244efade1fa754aa39fee
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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