Ethyl chloroformate → HCID 70415111, compound

HRID 845214Notes

Reaction equation

HRID 845214 reaction equation
[NH2:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[CH:4]=[CH:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22].[CH2:23]([O:25][C:26](Cl)=[O:27])[CH3:24]>N1C=CC=CC=1>[CH2:23]([O:25][C:26]([NH:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[CH:4]=[CH:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22])=[O:27])[CH3:24]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 13714626HCID 13714626, compound

Product 1

HCID 70415111HCID 70415111, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 3.0 g of 4-aminoandrosta-4,6-dien-3,17-dione in 15 ml of dry pyridine, cooled to 0° to -5° C., 1.25 ml of ethylchlorocarbonate are added dropwise. The mixture is cooled and stirred for 30 minutes and then, after the temperature is left to rise to 20° C., it is quenched in 100 ml of water. The mixture is extracted several times with ethyl acetate, washed with aqueous sodium chloride solution until neutral and dried. The solvent is then distilled in vacuo to obtaind 3.2 g of crude which is purified by crystallization with warm ethyl acetate to yield 2.95 g of pure title compound,

Workup

  1. temperatureThe mixture is cooled
  2. waitafter the temperature is left
  3. customto rise to 20° C.
  4. customit is quenched in 100 ml of water
  5. extractionThe mixture is extracted several times with ethyl acetate
  6. washwashed with aqueous sodium chloride solution until neutral and
  7. customdried
  8. distillationThe solvent is then distilled in vacuo
  9. customis purified by crystallization with warm ethyl acetate

Sources & evidence

ORD record
ord-7449a678186a412a8ae5ba4ae74a2976
Source dataset
uspto-grants-1988_07
Patent number
US04757061

Reaction notes

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