Benzoyl chloride → HCID 15838325, compound

HRID 1735153Notes

Reaction equation

HRID 1735153 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C:18]([NH:19][C:20](=[O:28])[CH2:21][CH2:22]1)=[CH:17][CH2:16]3)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>N1C=CC=CC=1.C(Cl)Cl>[C:29]([N:19]1[C:20](=[O:28])[CH2:21][CH2:22][C@@:23]2([CH3:24])[C:18]1=[CH:17][CH2:16][C@@H:15]1[C@@H:25]2[CH2:26][CH2:27][C@@:10]2([CH3:11])[C@H:12]1[CH2:13][CH2:14][C@@H:9]2[O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 15838324HCID 15838324, compound

Product 1

HCID 15838325HCID 15838325, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To 17β-t-butyldimethylsilyloxy-4-azaandrost-5-en-3-one (2 g) in pyridine (5 ml) at 5°-10° C. was added benzoyl chloride (2 ml) in CH2Cl2 (10 ml) dropwise. After the addition, the mixture was stirred at 60° C. for 3 hours and poured onto ice-water. The mixture was extracted with methylene chloride, and dried (Na2SO4). Removal of solvent gave the crude product which was recrystallized from CH2Cl2 -hexane to afford the title product.

Workup

  1. additionAfter the addition
  2. additionpoured onto ice-water
  3. extractionThe mixture was extracted with methylene chloride
  4. dry with materialdried (Na2SO4)
  5. customRemoval of solvent
  6. customgave the crude product which
  7. customwas recrystallized from CH2Cl2 -hexane

Sources & evidence

ORD record
ord-6041d640b4474c4e89be7c29928d7695
Source dataset
uspto-grants-1996_07
Patent number
US05536727

Reaction notes

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