2,2,2-Trichloroethyl chloroformate → HCID 12804701, compound

HRID 223430Notes

Reaction equation

HRID 223430 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].[NH2:10][C@@H:11]1[CH2:30][C@@:29]2([CH3:31])[C@@H:22]([CH2:23][CH2:24][C@@H:25]2[C:26](=[O:28])[CH3:27])[C@H:21]2[C@H:12]1[C@:13]1([CH3:36])[C@@H:18]([CH2:19][CH2:20]2)[CH2:17][C@H:16]([OH:32])[C@@H:15]([O:33][CH2:34][CH3:35])[CH2:14]1>N1C=CC=CC=1.O>[CH2:34]([O:33][C@H:15]1[CH2:14][C@@:13]2([CH3:36])[C@@H:18]([CH2:19][CH2:20][C@@H:21]3[C@@H:12]2[C@H:11]([NH:10][C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3])[CH2:30][C@@:29]2([CH3:31])[C@H:22]3[CH2:23][CH2:24][C@@H:25]2[C:26](=[O:28])[CH3:27])[CH2:17][C@@H:16]1[O:32][C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3])[CH3:35]

Participants

5

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformate2×HCID 70544367HCID 70544367, compound

Product 1

HCID 12804701HCID 12804701, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

2,2,2-Trichloroethyl chloroformate (1 ml) was added to a stirred solution of 11α-amino-2β-ethoxy-3α-hydroxy-5α-pregnan-20-one (2 g) in pyridine (20 ml). After 16 hours complete reaction was not obtained. A further quantity of 2,2,2-trichloroethyl chloroformate (1 ml) was added and after 30 minutes the mixture was diluted with water (30 ml). The mixture was extracted with ether (x 2) and the extracts were washed with 2 M-HCl (x 4) and water (x 2) and dried. Evaporation of the solution left a yellow froth which was purified by column chromatography on silica eluted with ethyl acetate:petrol (1:3) to give a solid (2.5 g). A portion was crystallised from ether/petrol to give the title compound m.p. 147°-149° C., [α]D +48°.

Workup

  1. customAfter 16 hours complete reaction
  2. customwas not obtained
  3. extractionThe mixture was extracted with ether (x 2)
  4. washthe extracts were washed with 2 M-HCl (x 4) and water (x 2)
  5. customdried
  6. customEvaporation of the solution
  7. waitleft a yellow froth which
  8. customwas purified by column chromatography on silica
  9. washeluted with ethyl acetate:petrol (1:3)

Sources & evidence

ORD record
ord-2164baceb5324e9abcda7838ab052b94
Source dataset
uspto-grants-1982_10
Patent number
US04353898

Reaction notes

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