Benzyl chloroformate → (S)-2-(((Benzyloxy)carbonyl)amino)-3-(1-methyl-1H-imidazol-4-yl)propanoic acid

HRID 355524ノート

反応式

HRID 355524 の反応式
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH3:12][N:13]1[CH:23]=[N:22][C:15]([CH2:16][C@@H:17]([C:19]([OH:21])=[O:20])[NH2:18])=[CH:14]1>C1COCC1.C([O-])(O)=O.[Na+]>[NH:18]([C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3])[C@H:17]([C:19]([OH:21])=[O:20])[CH2:16][C:15]1[N:22]=[CH:23][N:13]([CH3:12])[CH:14]=1

参加物

5

反応物 2

HCID 10387Benzyl chloroformateHCID 921051-Methyl-L-histidine

生成物 1

HCID 13490232(S)-2-(((Benzyloxy)carbonyl)amino)-3-(1-methyl-1H-imidazol-4-yl)propanoic acid収率 105.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Benzyl chloroformate (0.24 mL, 1.7 mmol) was added dropwise to a slurry of 1-methyl-L-histidine (0.25 g, 1.5 mmol) in THF (5 mL) and saturated aqueous NaHCO3, (5 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred overnight. The mixture was concentrated and diluted with H2O, washed with ether, and the pH adjusted to 6-7 with iN HCl. The mixture was concentrated, then diluted with CHCl3 (150 mL) and MeOH (15 mL), and stirred for 1 hour. The mixture was dried (MgSO4) and concentrated to provide 0.48 g of the title compound which was used without further purification.

後処理

  1. concentrationThe mixture was concentrated
  2. additiondiluted with H2O
  3. washwashed with ether
  4. concentrationThe mixture was concentrated
  5. additiondiluted with CHCl3 (150 mL) and MeOH (15 mL)
  6. stirringstirred for 1 hour
  7. dry with materialThe mixture was dried (MgSO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-e1458ba802774ad297b83086e0e7535f
出典データセット
uspto-grants-1998_11
特許番号
US05830868

反応ノート

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