Phenyl chloroformate → HCID 67043797, compound

HRID 601772Notes

Reaction equation

HRID 601772 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([S:21]([C:24]1[CH:25]=[CH:26][CH:27]=[C:28]3[C:33]=1[N:32]=[CH:31][CH:30]=[CH:29]3)(=[O:23])=[O:22])[C:16](=[O:34])[C:15]2([OH:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[O:41][CH3:42]>N1C=CC=CC=1>[C:5]1([O:4][C:2](=[O:3])[O:43][C:15]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[O:41][CH3:42])[C:14]3[C:18](=[CH:19][CH:20]=[C:12]([Cl:11])[CH:13]=3)[N:17]([S:21]([C:24]3[CH:25]=[CH:26][CH:27]=[C:28]4[C:33]=3[N:32]=[CH:31][CH:30]=[CH:29]4)(=[O:23])=[O:22])[C:16]2=[O:34])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 51037830HCID 51037830, compound

Product 1

HCID 67043797HCID 67043797, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phenyl chloroformate (0.35 ml, 2.79 mmol) was added dropwise to a solution of example 64 (300 mg, 0.624 mmol) in pyridine (6 ml) while cooling slightly. The reaction mixture was stirred at room temperature overnight. After addition of ice-water, the mixture was extracted with ethyl acetate, and the organic phase was washed several times with dilute citric acid solution and water. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The residue was triturated with diethyl ether, and the resulting precipitate was filtered off, washed with diethyl ether and dried. 310 mg of the desired intermediate were obtained.

Workup

  1. temperaturewhile cooling slightly
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed several times with dilute citric acid solution and water
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated with diethyl ether
  7. filtrationthe resulting precipitate was filtered off
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-5f6e3fadff254e10a66d2536c0f0ab0d
Source dataset
uspto-grants-2011_03
Patent number
US07902379B2

Reaction notes

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