Trifluoroacetic acid → HCID 44155671, compound

HRID 1253908Notes

Reaction equation

HRID 1253908 reaction equation
C(OC([NH:8][C@H:9]([CH2:30][C:31]1[CH:36]=[C:35]([F:37])[C:34]([F:38])=[CH:33][C:32]=1[F:39])[CH2:10][C:11]([N:13]1[CH2:22][C:21]2[N:17]([CH:18]=[N:19][C:20]=2[C:23]([OH:25])=[O:24])[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[CH2:14]1)=[O:12])=O)(C)(C)C.[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43]>C(Cl)Cl>[F:40][C:41]([F:46])([F:45])[C:42]([OH:44])=[O:43].[NH2:8][C@H:9]([CH2:30][C:31]1[CH:36]=[C:35]([F:37])[C:34]([F:38])=[CH:33][C:32]=1[F:39])[CH2:10][C:11]([N:13]1[CH2:22][C:21]2[N:17]([CH:18]=[N:19][C:20]=2[C:23]([OH:25])=[O:24])[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[CH2:14]1)=[O:12]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68777038HCID 68777038, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 44155671HCID 44155671, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)-5-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)butyryl]-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid (35 mg, 0.06 mmol) in dry DCM (5 mL), was added trifluoroacetic acid (6.18 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 evaporated in vacuo to afford a gummy solid was crystallised from hexane to afford trifluoroacetic acid salt of 5-[(R)-3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid (28 mg, 78%).

Workup

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

Sources & evidence

ORD record
ord-fe882bb1d3e14e3f84ec0daf5842732c
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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