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

HRID 1476256

Reaction equation

HRID 1476256 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-b232a949cecf434984cfd7d79f2f1d8f
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Linked notes

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