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

HRID 7272

反応式

HRID 7272 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-acb43fa5eb1b42d09e33b5d59c24f091
出典データセット
uspto-grants-2006_08
特許番号
US07084139B2

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