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

HRID 626636노트

반응식

HRID 626636 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9909599664b34a78bb72b203a343454e
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309207B2

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