Thionyl Chloride → (R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate

HRID 731551

반응식

HRID 731551 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:17]([OH:19])=[O:18])[CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O>C(OCC)(=O)C>[O:18]=[C:17]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)[CH2:13][C:14](=[O:16])[O:19]1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 5289152(2R)-2-(((benzyloxy)carbonyl)amino)butanedioic acid

생성물 1

HCID 12416472(R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate수율 99.8%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A stirred suspension of N-(benzyloxycarbonyl)-D-aspartic acid (14.7 g, 55.1 mmol) in ethyl acetate (100 mL) was treated dropwise with thionyl chloride (40 mL, 511 mmol) and the resulting homogeneous mixture was stirred at room temperature for 16 hours, and concentrated. The resulting solid was triturated in 1:1 diethyl ether/hexanes (200 mL) for 2 hours and filtered. The solid was dried to provide the desired product (13.7 g, 99%).

후처리

  1. concentrationconcentrated
  2. customThe resulting solid was triturated in 1:1 diethyl ether/hexanes (200 mL) for 2 hours
  3. filtrationfiltered
  4. customThe solid was dried

출처 및 근거

ORD 기록
ord-4e4a308926e9427e97248689f4001b41
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585858B2

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