Trifluoroacetic acid → HCID 21702192, compound

HRID 1596539

Reaction equation

HRID 1596539 reaction equation
C([O:5][C:6]([C:8]1[C:15]2[C:11]([N:12]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=3)[CH:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH:14]=2)=[CH:10][CH:9]=1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:6]([C:8]1[C:15]2[C:11]([N:12]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=3)[CH:13]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH:14]=2)=[CH:10][CH:9]=1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21702180Benzyl 4-tert-butoxycarbonyl-1-(3,4-dichlorobenzyl)cyclopenta[b]pyrrole-2-carboxylate

Product 1

HCID 21702192HCID 21702192, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl 4-tert-butoxycarbonyl-1-(3,4dichlorobenzyl)cyclopenta[b]pyrrole-2-carboxylate (0.7 g) was dissolved in methylene chloride (10 mL) and TFA (3 mL) was added. Stirring was continued for 24 hours and the solvents were removed in vacuo to afford a pale oil. The oil slowly solidified on standing to afford the title product (0.61 g, 98%), NMR d(DMSO) 2.40 (4H, m), 3.70 (1H, t), 5.10 (2H, s), 5.40 (2H, AB d), 6.70 (1H, s), 6.90 (1H, d), 7.30 (6H, m), 7.50 (1H, d); M/z (−) 444, 442 (M-H+).

Workup

  1. customthe solvents were removed in vacuo
  2. customto afford a pale oil

Sources & evidence

ORD record
ord-eddf44201f204b919c44a3656eca1bf0
Source dataset
uspto-grants-2001_09
Patent number
US06291507B1

Linked notes

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