Trifluoroacetic acid → (S)-methyl 5-(4-(benzyloxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

HRID 418366Notes

Reaction equation

HRID 418366 reaction equation
CC(OC([NH:8][C@@H:9]([CH2:14][CH2:15][C:16](=O)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)[C:10]([O:12][CH3:13])=[O:11])=O)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:25]1([CH2:24][O:23][C:20]2[CH:21]=[CH:22][C:17]([C:16]3[CH2:15][CH2:14][C@@H:9]([C:10]([O:12][CH3:13])=[O:11])[N:8]=3)=[CH:18][CH:19]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59164841methyl (2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-oxo-5-{4-[(phenylmethyl)oxy]phenyl}pentanoate

Product 1

HCID 59164837(S)-methyl 5-(4-(benzyloxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl(2S)-2-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-5-oxo-5-{4-[(phenylmethyl)oxy]phenyl}pentanoate (323 mg, 0.75 mmol) in dry DCM (4 ml) at 0° C., under nitrogen atmosphere was added trifluoroacetic acid (1 ml) dropwise. The resulting pale pink solution was allowed to warm to room temperature over 1 hour, then it was evaporated under reduced pressure, affording the title compound (D7, 291 mg, 0.68 mmol, 91%) as a greenish oil which may be used in the next step without any further purification; Rt (HPLC): 3.69 min; MS: (ES/+) m/z: 310 [MH+], C19H19NO3 requires 309.

Workup

  1. customit was evaporated under reduced pressure

Sources & evidence

ORD record
ord-34ad7dbd02934a3cbdff5b6338567c5e
Source dataset
uspto-grants-2012_01
Patent number
US08093268B2

Reaction notes

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