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Trifluoroacetic acid → HCID 57971633, compound

HRID 2360673
Notes
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Reaction equation

HRID 2360673 reaction equation
[CH:1]1([O:6][C:7](=[O:52])[C@@H:8]([N:15](C(OC(C)(C)C)=O)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]4[CH:32]=[C:31]([C:33](=[O:43])[NH:34][O:35]C(OCC(C)C)C)[S:30][C:29]=4[CH:44]=3)[CH:18]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO.C(Cl)Cl>[CH:1]1([O:6][C:7](=[O:52])[C@@H:8]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([NH:23][CH2:24][C:25]3[CH:26]=[CH:27][C:28]4[CH:32]=[C:31]([C:33](=[O:43])[NH:34][OH:35])[S:30][C:29]=4[CH:44]=3)[CH:18]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57971685HCID 57971685, compound

Product 1

HCID 57971633HCID 57971633, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of (S)-[tert-Butoxycarbonyl-(3-{[2-(1-isobutoxy-ethoxycarbamoyl)-benzo[b]thiophen-6-ylmethyl]-amino}-benzyl)-amino]-phenyl-acetic acid cyclopentyl ester (0.100 g, 0.14 mmol) in DCM/MeOH (1 ml:1 ml) was added TFA (8 ml). The solution was stirred for 2 h, then diluted with DCM (200 ml). The solution was washed with saturated sodium bicarbonate (100 ml). The solution was dried (Na2SO4), concentrated and purified by reverse phase HPLC to yield the desired product (8.1 mg, 11% yield). LCMS purity 98%, m/z 531 (M+H)+ 300 MHz, DMSO, δ:1.26-1.85 (8H, m), 3.47 (2H, s), 4.21 (1H, s), 4.38 (2H, d, J 5.8 Hz), 5.02-5.07 (1H, m), 6.32 (1H, t, J 6.0 Hz), 6.45 (2H, d, J 7.9 Hz), 6.57 (1H, s), 6.97 (1H, t, J 7.8 Hz), 7.23-7.35 (5H, m), 7.42 (1H, dd, J 1.2, 8.3 Hz), 7.84 (1H, s), 7.87 (1H, s), 7.93 (1H, s), 9.23 (1H, br s), 11.4 (1H, br s)

Workup

  1. washThe solution was washed with saturated sodium bicarbonate (100 ml)
  2. dry with materialThe solution was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-82f86e8c9bee4119868b6ce6f45ff90d
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08686032B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes