Trifluoroacetic acid → HCID 89580508, compound

HRID 74734Notes

Reaction equation

HRID 74734 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-63687cd6703646e299a803a6f3689956
Source dataset
uspto-grants-2014_09
Patent number
US08828401B2

Reaction notes

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