Trifluoroacetic acid → HCID 44155128, compound

HRID 1253885Notes

Reaction equation

HRID 1253885 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:31][C:32]1[CH:37]=[C:36]([F:38])[C:35]([F:39])=[CH:34][C:33]=1[F:40])[CH2:9][C:10]([N:12]1[CH2:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[N:15]([CH2:23][C:24](=[O:29])[NH:25][CH:26]2[CH2:28][CH2:27]2)[C:14](=[O:30])[CH2:13]1)=[O:11])(C)(C)C.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>C(Cl)Cl>[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[NH2:7][C@H:8]([CH2:31][C:32]1[CH:37]=[C:36]([F:38])[C:35]([F:39])=[CH:34][C:33]=1[F:40])[CH2:9][C:10]([N:12]1[CH2:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[N:15]([CH2:23][C:24]([NH:25][CH:26]2[CH2:28][CH2:27]2)=[O:29])[C:14](=[O:30])[CH2:13]1)=[O:11]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68640333HCID 68640333, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 44155128HCID 44155128, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [3-(1-cyclopropylcarbamoylmethyl-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-3-oxo-1-(2,4,5-trifluoro-benzyl)-propyl]-carbamic acid tert-butyl ester (40 mg, 0.07 mmol) in DCM (2 mL), was added trifluoroacetic acid (0.2 mL, 3 mL/mmol). The reaction mixture was stirred at r.t. for 1 h. After the completion of the reaction as confirmed by TLC, excess of trifluoroacetic acid and DCM were removed in vacuo to afford a gummy solid which was crystallised from hexane to afford trifluoroacetic acid salt of 2-{4-[(R)-3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-2-oxo-2,3,4,5-tetrahydro-benzo[e][1,4]diazepin-1-yl}-N-cyclopropyl-acetamide (32 mg, 78%).

Workup

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

Sources & evidence

ORD record
ord-8b4a8f8f527041e1b5a85a7a7b65d97d
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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