Sodium Bicarbonate → {3-[(Benzofuran-5-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester

HRID 2224670노트

반응식

HRID 2224670 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10](Cl)(=[O:12])=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[O:14]1[CH:18]2[O:19][CH2:20][CH2:21][CH:17]2[CH:16]([O:22][C:23](=[O:41])[NH:24][CH:25]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:26]([OH:33])[CH2:27][NH:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:15]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:14]1[CH:18]2[O:19][CH2:20][CH2:21][CH:17]2[CH:16]([O:22][C:23](=[O:41])[NH:24][CH:25]([CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:26]([OH:33])[CH2:27][N:28]([S:10]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH:2]=[CH:3][C:4]=3[CH:9]=2)(=[O:12])=[O:11])[CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:15]1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 21055240(1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl esterHCID 53403186Benzofuran-5-sulfonyl chloride

생성물 1

HCID 66769907{3-[(Benzofuran-5-sulfonyl)-isobutyl-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Benzofuran-5-sulfonyl chloride 148 mg (0.68 mmol) was dissolved in 5 mL of methylene chloride. (1-Benzyl-2-hydroxy-3-isobutylamino-propyl)-carbamic acid hexahydro-furo[2,3-b]furan-3-yl ester 19 (244 mg, 0.62 mmol) was added followed by 0.63 mL 10% NaHCO3 solution (0.75 mmol). The reaction was stirred at room temperature for 16 hours. The organic phase was separated and loaded onto silica gel in methylene chloride. The excess of benzofuran-5-sulfonyl chloride was washed out by several portions of methylene chloride. The final product was obtained by eluting with 3/1 ethyl acetate/methylene chloride. Concentration in vacuo afforded 350 mg (98.5% yield) of the final product with HPLC purity of >97% (220 nm). The product can be recrystallized from ethyl acetate/hexanes to get colorless crystals m.p. 122-124° C. MS 573 (MH)+.

후처리

  1. customThe organic phase was separated
  2. washThe excess of benzofuran-5-sulfonyl chloride was washed out by several portions of methylene chloride

출처 및 근거

ORD 기록
ord-9ab5b61a78ba4f0aa412002431a7f5c7
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378441B2

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