Trifluoroacetic acid → HCID 44156640, compound

HRID 1253881Notes

Reaction equation

HRID 1253881 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13](=[O:30])[CH2:14][C@H:15]([NH:26]C(=O)O)[CH2:16][C:17]2[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:18]=2[F:25])[CH2:4][C:3]1=[O:31].[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35]>C(Cl)Cl>[F:32][C:33]([F:38])([F:37])[C:34]([OH:36])=[O:35].[NH2:26][C@H:15]([CH2:16][C:17]1[CH:22]=[C:21]([F:23])[C:20]([F:24])=[CH:19][C:18]=1[F:25])[CH2:14][C:13]([N:5]1[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:2]([CH3:1])[C:3](=[O:31])[CH2:4]1)=[O:30]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 86648332HCID 86648332, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 44156640HCID 44156640, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2 [3-(1-methyl-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-3-oxo-(R)-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tart-butyl ester (90 mg 0.18 mmol) in dry DCM (5 mL), was added trifluoroacetic acid (0.55 mL, 3 mL/mmol). The reaction mixture was stirred at r.t. for 1 h. After completion of the reaction, as confirmed by TLC, excess of TFA and DCM were evaporated in vacuo to afford a gummy solid which was crystallised from hexane to afford trifluoroacetic acid salt of 4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)-butyryl]-1-methyl-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (70 mg, 76%) as a white solid

Workup

  1. customAfter completion of the reaction
  2. customwere evaporated in vacuo
  3. customto afford a gummy solid which
  4. customwas crystallised from hexane

Sources & evidence

ORD record
ord-2afae34f6a804ead9da15e9cc7ac9d46
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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