L-Methionine → tert-Butyl N-[(benzyloxy)carbonyl]-L-methionyl-L-alaninate

HRID 33420

반응식

HRID 33420 반응식
[NH2:1][C@H:2]([C:7]([OH:9])=O)[CH2:3][CH2:4][S:5][CH3:6].Cl.CN(C)CCCN=C=NCC.[CH:22]1[CH:23]=[CH:24][C:25]2N(O)N=N[C:26]=2[CH:27]=1.[C:32]([O:36][C:37](=[O:41])[C@H:38]([CH3:40])[NH2:39])([CH3:35])([CH3:34])[CH3:33]>CN(C=O)C.C(N(CC)CC)C>[CH2:32]([O:36][C:37]([NH:1][C@H:2]([C:7]([NH:39][C@H:38]([C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:41])[CH3:40])=[O:9])[CH2:3][CH2:4][S:5][CH3:6])=[O:41])[C:26]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:27]=1

참가 물질

7

반응물 4

HCID 6137L-MethionineHCID 757711-HydroxybenzotriazoleHCID 89016L-Alanine 1,1-dimethylethyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 16124765tert-Butyl N-[(benzyloxy)carbonyl]-L-methionyl-L-alaninate수율 109.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

Z-Protected L-methionine (10 g) was dissolved in DMF (200 ml) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (8.13 g) was added followed by HOBT (5.72 g) and triethylamine (19.7 ml). The mixture was stirred for 1 h then L-alanine tert-butyl ester (7.7 g) was added and stirring continued for 18 h. The mixture was concentrated under reduced pressure and partitioned between diethyl ether and water. The separated organic phase was washed with hydrochloric acid (1M), saturated sodium bicarbonate solution and brine, dried (over magnesium sulphate) and concentrated under reduced pressure to give the title compound (11.9 g) as an orange oil which crystallised on standing.

후처리

  1. stirringstirring
  2. waitcontinued for 18 h
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custompartitioned between diethyl ether and water
  5. washThe separated organic phase was washed with hydrochloric acid (1M), saturated sodium bicarbonate solution and brine
  6. dry with materialdried (over magnesium sulphate)
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-5eb15583d29d4596b2376fa164d946a4
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429587B2

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