Hydrochloric Acid → (R)-3-(1-Allyl-1H-imidazol-4-yl)-2-benzyloxycarbonylaminopropionic acid

HRID 2274547ノート

反応式

HRID 2274547 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].[CH2:12]([N:15]1[CH:19]=[C:18]([CH2:20][C@@H:21]([NH2:25])[C:22]([OH:24])=[O:23])[N:17]=[CH:16]1)[CH:13]=[CH2:14].C(OCC)(=O)C.Cl>[OH-].[Na+]>[CH2:12]([N:15]1[CH:19]=[C:18]([CH2:20][C@@H:21]([NH:25][C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[C:22]([OH:24])=[O:23])[N:17]=[CH:16]1)[CH:13]=[CH2:14]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 67319867(R)-3-(1-allyl-1H-imidazol-4-yl)-2-aminopropionic acid

生成物 1

HCID 67029144(R)-3-(1-Allyl-1H-imidazol-4-yl)-2-benzyloxycarbonylaminopropionic acid

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒2 回

実験手順

3.53 ml (4.24 g, 24.84 mmol) of benzyl chloroformate were added to a solution of 4.85 g (24.84 mmol) of (R)-3-(1-allyl-1H-imidazol-4-yl)-2-aminopropionic acid (as described for the (S)-enantiomer in Bioorg. Med. Chem. 2006, 14, 5981-5988) in 13 ml of 2N sodium hydroxide solution while stirring at 0° C., and stirring was continued at this temperature with addition of a further 13 ml of 2N sodium hydroxide solution for 2 h, and the mixture was them warmed to RT. The reaction mixture was covered with a layer of ethyl acetate, and the pH was adjusted to 3 to 4 with 6N hydrochloric acid. The organic phase was separated off, and the aqueous phase was washed again with ethyl acetate and then freeze dried. The residue was mixed with THF and DMF until stirrable and was thoroughly stirred, and the suspension was filtered. The resulting solution was concentrated and reacted without further purification in the next step.

後処理

  1. customThe organic phase was separated off
  2. washthe aqueous phase was washed again with ethyl acetate
  3. customfreeze dried
  4. additionThe residue was mixed with THF and DMF until stirrable and
  5. stirringwas thoroughly stirred
  6. filtrationthe suspension was filtered
  7. concentrationThe resulting solution was concentrated
  8. customreacted without further purification in the next step

出典と根拠

ORDレコード
ord-39c53d822b104308877ec857026f9435
出典データセット
uspto-grants-2015_09
特許番号
US09126955B2

反応ノート

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