Acetic Anhydride → (R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate

HRID 1771157

반응식

HRID 1771157 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:16][C:17]([OH:19])=[O:18])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C>>[O:15]=[C:13]1[C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:16][C:17](=[O:18])[O:19]1

참가 물질

3

반응물 2

HCID 7918Acetic AnhydrideHCID 5289152(2R)-2-(((benzyloxy)carbonyl)amino)butanedioic acid

생성물 1

HCID 12416472(R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate

실험 절차

A mixture of (R)-2-(benzyloxycarbonylamino)succinic acid (Aldrich, 30 g, 112.26 mmol) and acetic anhydride (65.7 ml, 696.02 mmol) was stirred overnight at room temperature during which time the reaction mixture became clear. The volatiles were removed under reduced pressure (water bath temperature 65° C.) and the concentrate was azeotroped with toluene (3×50 ml) and obtained the title product after drying for ˜48 hours at 60° C. under high vacuum pump (28.0 g, yield: almost quantitative).

후처리

  1. customThe volatiles were removed under reduced pressure (water bath temperature 65° C.)
  2. customthe concentrate was azeotroped with toluene (3×50 ml)

출처 및 근거

ORD 기록
ord-15c6514df02a42ef813e31428df4ff93
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09248140B2

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