Trifluoroacetic acid → HCID 44137546, compound

HRID 1253873Notes

Reaction equation

HRID 1253873 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:24][C:25]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:26]=1[F:33])[CH2:9][C:10](=[O:23])[N:11]1[CH2:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[NH:14][C:13](=[O:22])[CH2:12]1)(C)(C)C.[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].CCCCCC>C(Cl)Cl>[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38].[NH2:7][C@H:8]([CH2:24][C:25]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:26]=1[F:33])[CH2:9][C:10]([N:11]1[CH2:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[NH:14][C:13](=[O:22])[CH2:12]1)=[O:23]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acid2×HCID 8058HexaneHCID 68777518HCID 68777518, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 44137546HCID 44137546, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [(R)-3-oxo-3-(2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester (40 mg, 0.08 mmol) in DCM (5 mL), was added trifluoroacetic acid (0.24 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 trifluoroacetic acid and DCM were evaporated in vacuo to afford a gummy solid which was solidified from hexane to afford trifluoroacetic acid salt of 4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)-butyryl]-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (30 Mg, 73%) as a solid.

Workup

  1. customAfter completion of the reaction
  2. customwere evaporated in vacuo
  3. customto afford a gummy solid which

Sources & evidence

ORD record
ord-30727d571670490ba200221355e152e9
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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