methyl (S)-lactate → methyl 2-(R)-{[-4-(4-chlorophenyl)piperazine-1-sulfonyl]amino}propionate

HRID 1856865Notes

Reaction equation

CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([S:20]([NH2:23])(=[O:22])=[O:21])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[O-]S(C(F)(F)F)(=O)=O.[C:32]([O:37][CH3:38])(=[O:36])[C@H:33]([CH3:35])O>O1CCCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([S:20]([NH:23][C@H:33]([CH3:35])[C:32]([O:37][CH3:38])=[O:36])(=[O:22])=[O:21])[CH2:16][CH2:15]2)=[CH:12][CH:13]=1

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of potassium tert-butoxide (0.87 ml, 1M in tetrahydrofuran) was added to a solution of [4-(4-chlorophenyl)piperazine-1-sulfonyl]amine (200 mg, 0.73 mmol), [prepared as described in Step 1 above], in tetrahydrofuran (10 ml) at -60° C. After 10 min., a solution of the triflate derivative of methyl (S)-lactate (604 mg, 2.56 mmol) in tetrahydrofuran (3 ml) was added and the reaction mixture was allowed to warm to -30° C. over 30 min. The reaction mixture was quenched with saturated ammonium chloride and the product was extracted into ethyl acetate. The solvent was removed in vacuo and the residue was chromatographed (SiO2, 30% ethyl acetate/hexane) to give methyl 2-(R)-{[-4-(4-chlorophenyl)piperazine-1-sulfonyl]amino}propionate as a colorless oil (66%).

Workup

customThe reaction mixture was quenched with saturated ammonium chloride
extractionthe product was extracted into ethyl acetate
customThe solvent was removed in vacuo
customthe residue was chromatographed (SiO2, 30% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-25e7dd9fe92d4d6f91777b0c6a7c481d
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143744

Reaction notes

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