Butanoic acid, 4-chloro-, methyl ester → HCID 22897426, compound
Reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:20][CH2:19][C@@H:18]([CH2:21][NH:22][CH3:23])[C@@H:17]2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl[CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38].CCN(C(C)C)C(C)C>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:11][C:9]([F:12])([F:10])[C:7]1[CH:6]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:20][CH2:19][C@@H:18]([CH2:21][N:22]([CH2:34][CH2:35][CH2:36][C:37]([O:39][CH3:40])=[O:38])[CH3:23])[C@@H:17]2[C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH3:14])[CH:4]=[C:3]([C:2]([F:1])([F:31])[F:32])[CH:8]=1Participants
6
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 65 mg of 1-(S)-(1-(R)-(3,5-bis(trifluoromethyl)-phenyl)ethoxy)-2-(R)-(4-fluorophenyl)-3-(R)-((methylamino)methyl)cyclopentane from Example 18, Step B in 1 mL of acetonitrile was added 0.019 mL of methyl 4-chlorobutyrate and 0.037 mL of DIPEA. The reaction was heated at 50° C. for 48 hours, then an additional 0.038 mL of methyl 4-chlorobutyrate, 0.074 mL of DIPEA and 3 mg of tetrabutylammonium iodide were added and heating continued at 70° C. for 48 hours. The reaction was evaporated under a stream of nitrogen and the residue purified by prep TLC (10% methanol in ethyl acetate) to give 41 mg of title compound and 17 mg of recovered starting material. Mass spec (ESI): 564 (M+1).
Workup
- temperatureheating
- customThe reaction was evaporated under a stream of nitrogen
- customthe residue purified by prep TLC (10% methanol in ethyl acetate)
Sources & evidence
- ORD record
- ord-409f641db2504f5cb93faa07bf3450bf
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479518B2
Reaction notes
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