Butanoic acid, 4-chloro-, methyl ester → HCID 22897434, compound

HRID 1017768Notes

Reaction equation

[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:20][CH2:19][C@@H:18]([NH:21][CH3:22])[C@@H:17]2[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl[CH2:33][CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37].CCN(C(C)C)C(C)C>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:20][CH2:19][C@@H:18]([N:21]([CH2:33][CH2:34][CH2:35][C:36]([O:38][CH3:39])=[O:37])[CH3:22])[C@@H:17]2[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH3:14])[CH:4]=[C:3]([C:2]([F:1])([F:30])[F:31])[CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 40 mg of 1-(S)-(1-(R)-(3,5-bis(trifluoromethyl)phenyl)ethoxy)-2-(S)-(4-fluorophenyl)-3-(R)-(methylamino)cyclopentane from Example 15 in 1 mL of acetonitrile was added 0.011 mL of methyl 4-chlorobutyrate and 0.046 mL of DIPEA. The reaction was heated at 50° C. for 24 hours, then an additional 0.022 mL of methyl 4-chlorobutyrate, 0.030 mL of DIPEA and 3 mg of tetrabutylammonium iodide were added and heating continued at 80° C. for 60 hours. The reaction was evaporated under a stream of nitrogen and the residue purified by prep TLC (5% methanol in methylene chloride) to give 27 mg of title compound. Mass spec (ESI): 550 (M+1).

Workup

temperatureheating
customThe reaction was evaporated under a stream of nitrogen
customthe residue purified by prep TLC (5% methanol in methylene chloride)

Sources & evidence

ORD record: ord-1b356054a5f8485f942d8ff2ece21837
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479518B2

Reaction notes

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