1-Chloroethyl chloroformate → HCID 136333277, compound

HRID 915991Notes

Reaction equation

HRID 915991 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[NH:21][C:22](=[O:36])[C:23]4[N:28]([CH:29]5[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]5)[N:27]=[C:26]([CH3:35])[C:24]=4[N:25]=3)=[C:16]([O:37][CH3:38])[CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:39]C(OC(Cl)C)=O>ClCCCl>[ClH:39].[CH:29]1([N:28]2[C:23]3[C:22](=[O:36])[NH:21][C:20]([C:17]4[CH:18]=[CH:19][C:14]([C:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=5)=[CH:15][C:16]=4[O:37][CH3:38])=[N:25][C:24]=3[C:26]([CH3:35])=[N:27]2)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 136005852HCID 136005852, compound

Product 1

HCID 136333277HCID 136333277, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a 10 ml 1,2-dichloroethane solution of 80 mg (0.16 mmol) of the compound obtained in Example 272, 25.4 μl (0.24 mmol) of 1-chloroethyl chloroformate was added, and the mixture was heated under reflux for 40 minutes. Then, the reaction mixture was returned to room temperature, and concentrated under reduced pressure. Methanol (10 ml) was added to the residue, and the mixture was heated under reflux for 20 minutes. The reaction mixture was returned to room temperature, and concentrated under reduced pressure. Precipitated solids were washed with methanol/ether=1/4 to obtain 43 mg (60%) of the captioned compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 40 minutes
  3. customwas returned to room temperature
  4. concentrationconcentrated under reduced pressure
  5. additionMethanol (10 ml) was added to the residue
  6. temperaturethe mixture was heated
  7. temperatureunder reflux for 20 minutes
  8. customwas returned to room temperature
  9. concentrationconcentrated under reduced pressure
  10. customPrecipitated solids
  11. washwere washed with methanol/ether=1/4

Sources & evidence

ORD record
ord-6da9a8514d3a4c08936df81e3564bfdc
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

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