4-Methylmorpholine → N-Boc-(2S,3S)-(-)-2-Amino-3-methyl-1-pentanol

HRID 427382

반응식

HRID 427382 반응식
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7](O)=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].CN1CCOCC1.ClC(OCC(C)C)=O>COCCOC>[C:10]([NH:1][C@H:2]([CH2:7][OH:8])[C@H:3]([CH2:5][CH3:6])[CH3:4])([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11]

참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 2724762tert-Butoxycarbonyl-L-isoleucine

생성물 1

HCID 14237729N-Boc-(2S,3S)-(-)-2-Amino-3-methyl-1-pentanol수율 92.2%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

In 5 ml of 1,2-dimethoxyethane (DME), 1.201 g of Boc-Ile-OH.1/2H2O was dissolved and 550 μl of N-methylmorpholine and 650 μl of isobutyl chloroformate were successively added dropwise at −15° C. After stirring for 1 min, the formed N-methylmorpholine hydrochloride was filtered off and washed twice with 2.5 ml each of DME. The filtrate and washings were combined and 284 mg of sodium borohydride in 2.5 ml of water was added in one portion. After 30 sec, 125 ml of water was added and the mixture was extracted with 25 ml of ethyl acetate and dried over anhydrous sodium sulfate. The dried solution was evaporated under reduced pressure to give 1.040 g of the title compound.

후처리

  1. dissolution1/2H2O was dissolved
  2. filtrationthe formed N-methylmorpholine hydrochloride was filtered off
  3. washwashed twice with 2.5 ml each of DME
  4. addition284 mg of sodium borohydride in 2.5 ml of water was added in one portion
  5. waitAfter 30 sec
  6. addition125 ml of water was added
  7. extractionthe mixture was extracted with 25 ml of ethyl acetate
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe dried solution was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-72b98dec643b46d8ac77cd6fa3033ca8
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313094B1

연결된 노트

불러오는 중…