4-Methylmorpholine → N-[(benzyloxy)carbonyl]-3-[(1-propylbutyl)sulfonyl)alanine

HRID 348851노트

반응식

HRID 348851 반응식
[CH2:1]([CH:4]([S:8]([CH2:11][C@@H:12]([C:14]([OH:16])=[O:15])[NH2:13])(=[O:10])=[O:9])[CH2:5][CH2:6][CH3:7])[CH2:2][CH3:3].[C:17](NC(=O)CCC(N)=O)([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].CN1CCOCC1>C(Cl)Cl>[CH2:20]([O:19][C:17]([NH:13][C@H:12]([C:14]([OH:16])=[O:15])[CH2:11][S:8]([CH:4]([CH2:5][CH2:6][CH3:7])[CH2:1][CH2:2][CH3:3])(=[O:9])=[O:10])=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 54145340N-CBZ succinamideHCID 574872803-[(1-Propylbutyl)sulfonyl]alanine

생성물 1

HCID 57508140N-[(benzyloxy)carbonyl]-3-[(1-propylbutyl)sulfonyl)alanine수율 109.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

A 250 ml round bottom flask equipped with magnetic stir bar and N2 inlet was charged with 7.8 g (27 mmole) 3-[(1-propylbutyl)sulfonyl]alanine and 7.4 g (30 mmole) N-Cbz succinamide in 100 ml methylene chloride. The reaction was cooled to 0° C., and 6.9 g NMM was added dropwise. The reaction was allowed to warm to room temperature and stirred for 4 hours at which point HPLC analysis indicated complete reaction. The reaction was concentrated in vacuo and partitioned between ethyl acetate and 1 N HCl. The organic layer was washed with water, brine, dried over sodium sulfate, and concentrated in vacuo to give 11.4 g of N-[(benzyloxy)carbonyl]-3-[(1-propylbutyl)sulfonyl]alanine that was used without further purification. M+H=386.

후처리

  1. customA 250 ml round bottom flask equipped with magnetic stir bar and N2 inlet
  2. temperatureto warm to room temperature
  3. customreaction
  4. concentrationThe reaction was concentrated in vacuo
  5. custompartitioned between ethyl acetate and 1 N HCl
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e36de91bfe3e47f4bcf9ac87a86510cd
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176242B2

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