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

HRID 731551

反応式

HRID 731551 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-4e4a308926e9427e97248689f4001b41
出典データセット
uspto-grants-2009_09
特許番号
US07585858B2

関連ノート

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