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

HRID 731551

Reaction equation

HRID 731551 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-4e4a308926e9427e97248689f4001b41
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Linked notes

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