Methanol → Methyl 2-[4-bromophenylsulfonyl]amino-3-phenylmethoxy-4-pentenoate

HRID 413404노트

반응식

HRID 413404 반응식
CC(C)(OC([NH:7][CH:8]([CH:12]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:13]=[CH2:14])[C:9]([OH:11])=[O:10])=O)C.S(Cl)(Cl)=O.[Br:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.[CH3:39]O>C(Cl)Cl.C(N(CC)CC)C>[Br:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH:7][CH:8]([CH:12]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:13]=[CH2:14])[C:9]([O:11][CH3:39])=[O:10])(=[O:37])=[O:36])=[CH:31][CH:30]=1

참가 물질

7

반응물 4

HCID 887MethanolHCID 7396p-Bromobenzenesulfonyl chlorideHCID 24386Thionyl ChlorideHCID 235082632-[(1,1-Dimethylethoxy)carbonyl]amino-3-phenylmethoxy-4pentenoic acid

생성물 1

HCID 23508255Methyl 2-[4-bromophenylsulfonyl]amino-3-phenylmethoxy-4-pentenoate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

The 2-[[1,1-dimethylethoxy)carbonyl]amino-3-phenylmethoxy-4-pentenoic acid 63b (1.8 g, 5.37 mmol) is dissolved in methanol (54 mL) and thionyl chloride (8.3 mL) is added dropwise to the mixture. The resulting mixture is stirred at room temperature until the reaction is complete by tlc. The crude reaction is dried and re-evaporated from methanol (3 times). The dried reaction mixture is taken up in methylene chloride (30 mL) and triethylamine (7 mL). 4-Bromophenylsulfonyl chloride (1.23 g, 4.83 mmol) is added and the reaction is stirred overnight. The solvent is removed in vacuo and the oil is taken up in ethyl acetate, and then washed consecutively with 1N HCl, saturated sodium bicarbonate solution, and finally with brine, then dried over magnesium sulfate and the solvent removed in vacuo. The crude material is adsorbed onto silica gel and purified over a silica column eluting with hexane followed with hexane:ethyl acetate (8:2). Product fractions are combined and dried to give the desired product.

후처리

  1. customThe crude reaction
  2. customis dried
  3. customre-evaporated from methanol (3 times)
  4. customThe dried reaction mixture
  5. stirringthe reaction is stirred overnight
  6. customThe solvent is removed in vacuo
  7. washwashed consecutively with 1N HCl, saturated sodium bicarbonate solution
  8. dry with materialfinally with brine, then dried over magnesium sulfate
  9. customthe solvent removed in vacuo
  10. custompurified over a silica column
  11. washeluting with hexane
  12. customdried

출처 및 근거

ORD 기록
ord-2c9d4ee15bab48a9bd44e1fc96b172ec
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566381B1

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