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

HRID 366476노트

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HRID 366476 반응식
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

참가 물질

6

반응물 4

HCID 94386methyl (S)-lactateHCID 2758875TrifluoromethanesulfonateHCID 22615685[4-(4-Chlorophenyl)piperazine-1-sulfonyl]amineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 18727241methyl 2-(R)-{[-4-(4-chlorophenyl)piperazine-1-sulfonyl]amino}propionate수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-30 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-249d6c18dcc5493ebc7b1db4c989e9c5
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06130220

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