Trifluoroacetic acid → HCID 68283799, compound

HRID 1527551Notes

Reaction equation

HRID 1527551 reaction equation
C([O:5][C:6](=[O:41])[CH2:7][C:8]1[CH:16]=[C:15]2[C:11]([C:12]([NH:20][C:21]([N:23]3[C@H:28]([C:29](=[O:40])[NH:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=4[F:39])[CH2:27][C@@H:26]4[C@H:24]3[CH2:25]4)=[O:22])=[CH:13][N:14]2[C:17](=[O:19])[NH2:18])=[CH:10][CH:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:17]([N:14]1[C:15]2[C:11](=[CH:10][CH:9]=[C:8]([CH2:7][C:6]([OH:41])=[O:5])[CH:16]=2)[C:12]([NH:20][C:21]([N:23]2[C@H:28]([C:29](=[O:40])[NH:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[C:33]=3[F:39])[CH2:27][C@@H:26]3[C@H:24]2[CH2:25]3)=[O:22])=[CH:13]1)(=[O:19])[NH2:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57520253HCID 57520253, compound

Product 1

HCID 68283799HCID 68283799, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

to a solution of (1-carbamoyl-3-{[(1R,3S,5R)-3-(3-chloro-2-fluoro-benzylcarbamoyl)-2-aza-bicyclo[3.1.0]hexane-2-carbonyl]-amino}-1H-indol-6-yl)-acetic acid tert-butyl ester Example 127 (30 mg, 0.051 mmol) in CH2Cl2 (0.5 mL) was added TFA (157 μL, 2.05 mmol) and the mixture was stirred at RT for 1 h. Then concentrated and the crude residue was taken up in Et2O and filtered-off to give the desired material. MS (UPLC): 528.2/530.3 [M+H]+, 1055.6/1057.2 [2M+H]+, 483.1/485.1 [M−CONH2]−, 1053.6/1055.6 [2M−H]−; tR (HPLC conditions f): 1.75 min.

Workup

  1. concentrationThen concentrated

Sources & evidence

ORD record
ord-3ec8dbf23d2c430da489211b3c3c0d19
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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