Trifluoroacetic acid → N-[3-[2,3-dichloro-4-(2-methylene-1-oxobutyl) phenoxy] acetylthio-2methylpropanoyl]-N-cyclopentyl glycine

HRID 543264Notes

Reaction equation

HRID 543264 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][N:8]([C:14](=[O:37])[CH:15]([CH3:36])[CH2:16][S:17][C:18](=[O:35])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:32])[C:28](=[CH2:31])[CH2:29][CH3:30])=[C:23]([Cl:33])[C:22]=1[Cl:34])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:34][C:22]1[C:23]([Cl:33])=[C:24]([C:27](=[O:32])[C:28](=[CH2:31])[CH2:29][CH3:30])[CH:25]=[CH:26][C:21]=1[O:20][CH2:19][C:18]([S:17][CH2:16][CH:15]([CH3:36])[C:14]([N:8]([CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]1)[CH2:7][C:6]([OH:38])=[O:5])=[O:37])=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20205973N-[3-[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetylthio-2-methylpropanoyl]-N-cyclopentyl glycine t-butyl ester

Product 1

HCID 54345300N-[3-[2,3-dichloro-4-(2-methylene-1-oxobutyl) phenoxy] acetylthio-2methylpropanoyl]-N-cyclopentyl glycineYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 5.2 g (8.7 mmol) of N-[3-[2,3-dichloro-4-(2-methylene-1-oxobutyl)phenoxy]acetylthio-2-methylpropanoyl]-N-cyclopentyl glycine t-butyl ester in 100 ml of methylene chloride was added 9.0 ml (117 mmol) of trifluoroacetic acid. After 12 hours the reaction mixture was carefully concentrated in vacuo and the residue was chromatographed via HPLC [methylene chloride/ether/acetic acid (88/10/2.5)]to afford 2.4 g (52%) of N-[3-[2,3-dichloro-4-(2-methylene-1-oxobutyl) phenoxy] acetylthio-2methylpropanoyl]-N-cyclopentyl glycine as a glass.

Workup

  1. concentrationAfter 12 hours the reaction mixture was carefully concentrated in vacuo
  2. customthe residue was chromatographed via HPLC [methylene chloride/ether/acetic acid (88/10/2.5)]to

Sources & evidence

ORD record
ord-fa4e4d7d006c4659b224f33f978a0bf3
Source dataset
uspto-grants-1987_04
Patent number
US04661515

Reaction notes

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