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

HRID 1771157

Reaction equation

HRID 1771157 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-15c6514df02a42ef813e31428df4ff93
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Linked notes

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