Trifluoroacetic acid → HCID 89580508, compound

HRID 2282818Notes

Reaction equation

HRID 2282818 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]3([C:24]([NH:26][C@H:27]([C:31]([N:33]([CH3:50])[C@@H:34]([C@@H:46]([CH3:49])[CH2:47][CH3:48])[C@H:35]([O:44][CH3:45])[CH2:36][C:37]([O:39]C(C)(C)C)=[O:38])=[O:32])[CH:28]([CH3:30])[CH3:29])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>ClCCl>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C:19]3([C:24]([NH:26][C@H:27]([C:31]([N:33]([CH3:50])[C@@H:34]([C@@H:46]([CH3:49])[CH2:47][CH3:48])[C@H:35]([O:44][CH3:45])[CH2:36][C:37]([OH:39])=[O:38])=[O:32])[CH:28]([CH3:29])[CH3:30])=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23]3)=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131731846tert-butyl (3R,4S,55)-4-[{N-[(1-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentyl)carbonyl]-L-valyl}(methyl)amino]-3-methoxy-5-methylheptanoate

Product 1

HCID 89580508HCID 89580508, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of #27 (500 mg, 0.723 mmol) in dichloromethane (7 mL, 0.1 M) was added trifluoroacetic acid (3 mL). The reaction mixture initially became orange, then darkened over time. After stirring for 18 hours, the solvent was removed in vacuo to give #28 (460 mg, quantitative) as a dark brown glass, which was used without further purification. LC-MS: m/z 636.3 [M+H+].

Workup

  1. customthe solvent was removed in vacuo
  2. customto give #28 (460 mg, quantitative) as a dark brown glass, which
  3. customwas used without further purification

Sources & evidence

ORD record
ord-932c2b52e07841eda2d9d672ebc1c607
Source dataset
uspto-grants-2015_09
Patent number
US09138486B2

Reaction notes

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