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

HRID 854287Notes

Reaction equation

HRID 854287 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 was stirred overnight at rt, 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, and the resulting product was washed with a small volume of ether and dried.

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. washthe resulting product was washed with a small volume of ether
  8. customdried

Sources & evidence

ORD record
ord-321a90361cf4491e8cf6c46c6baf3b00
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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