Water → 2,5-Dioxopyrrolidin-1-yl (4-methylbenzyl) carbonate

HRID 1827112Notes

Reaction equation

HRID 1827112 reaction equation
[C:1](=[O:18])([O:10][N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17])[O:2]N1C(=O)CCC1=O.[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]O)=[CH:22][CH:21]=1.O.CCOCC>CC#N.C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][O:2][C:1](=[O:18])[O:10][N:11]2[C:12](=[O:17])[CH2:13][CH2:14][C:15]2=[O:16])=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 115054-Methylbenzyl alcoholHCID 676246Di(succinimido) carbonate

Product 1

HCID 111399512,5-Dioxopyrrolidin-1-yl (4-methylbenzyl) carbonate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Disuccinimidyl carbonate (5.03 g, 19.65 mmol) in 30 mL MeCN and 30 mL DCM was treated with 4-methylbenzyl alcohol (2.4 g, 19.6 mmol) followed by DMAP (1.20 g, 9.82 mmol). The resulting cloudy reaction mixture cleared over 2 min, stirred overnight at rt, then poured into 100 mL water and partitioned. The organic layer was dried over anhydrous sodium sulfate and the solvent evaporated. The solid thus obtained was stirred with approx. 25 mL ether, filtered, washed with a small volume of ether and dried to yield carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 4-methyl-benzyl ester as a white solid. Ref: Chem. Pharm. Bull., 38(1):110–115 (1990).

Workup

  1. customThe resulting cloudy reaction mixture
  2. custompartitioned
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent evaporated
  5. customThe solid thus obtained
  6. filtrationfiltered
  7. washwashed with a small volume of ether
  8. customdried

Sources & evidence

ORD record
ord-27ffaaa087204159a6fe7a2db2853615
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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