Water → Benzyl carbamate

HRID 1455328Notes

Reaction equation

HRID 1455328 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H]1[C@H](C(O)=O)CC=CC1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:10])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 2733678HCID 2733678, compound

Product 1

HCID 12136Benzyl carbamateYield 155.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation A1, Step 3: A sample of (1R,6S)-6-benzyloxycarbonylamino-cyclohex-3-enecarboxylic acid (72 g) was dissolved in CH2Cl2 (750 mL) prior to the addition of CDI (50.9 g). After 2.5 h water was added, and the solution was extracted with CH2Cl2. The combined organic layers were dried, filtered, and concentrated. The resulting material was dissolved in CH2Cl2 and ammonia gas was bubbled through the solution for 1.5 h. After stirring overnight, the majority of the solvent was removed and Et2O was added. The product precipitated as a white solid and was collected to give (1R,6S)-6-carbamoyl-cyclohex-3-enyl)-carbamic acid benzyl ester (61.5 g). MS found: (M+H)+=275.3.

Workup

  1. extractionthe solution was extracted with CH2Cl2
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe resulting material was dissolved in CH2Cl2
  6. customammonia gas was bubbled through the solution for 1.5 h
  7. customthe majority of the solvent was removed
  8. additionEt2O was added
  9. customThe product precipitated as a white solid
  10. customwas collected

Sources & evidence

ORD record
ord-04091c63815347559d903414c361babe
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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