Benzoyl chloride → HCID 11285024, compound

HRID 895848Notes

Reaction equation

HRID 895848 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1([CH3:45])[C@@H:41]([OH:42])[CH2:40][CH2:39][C@@:38]2([CH3:43])[C:12]1=[CH:13][CH2:14][C@@H:15]1[C@@H:37]2[CH2:36][CH2:35][C@@:34]2([CH3:44])[C@H:16]1[CH2:17][CH2:18][C@@H:19]2[C@@H:20]([CH2:22][O:23][Si:24]([CH:31]([CH3:33])[CH3:32])([CH:28]([CH3:30])[CH3:29])[CH:25]([CH3:27])[CH3:26])[CH3:21]>>[C:1]([O:42][C@H:41]1[CH2:40][CH2:39][C@@:38]2([CH3:43])[C:12](=[CH:13][CH2:14][C@@H:15]3[C@@H:37]2[CH2:36][CH2:35][C@@:34]2([CH3:44])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C@@H:20]([CH2:22][O:23][Si:24]([CH:25]([CH3:26])[CH3:27])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])[CH3:21])[C:11]1([CH3:10])[CH3:45])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 7412Benzoyl chlorideHCID 11386782HCID 11386782, compound

Product 1

HCID 11285024HCID 11285024, compound

Procedure

34.4 ml of benzoylchloride were added to a solution of 70 g crude (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5-en-3β-ol (Example 1c) (not purified by chromatography) in 670 mg pyridine at 0-3° C. The reaction mixture was stirred for 2 h at room temperature and poured into ice-water. The precipitate was filtered off, washed with water and recrystallized from acetone to give 42 g of (20S)-4,4-dimethyl-20-[((triisopropylsilyl)oxy)methyl]-pregna-5-en-3β-ol benzoate.

Workup

  1. custompurified by chromatography) in 670 mg pyridine at 0-3° C
  2. additionpoured into ice-water
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customrecrystallized from acetone

Sources & evidence

ORD record
ord-a9bddab21dd949f080f3e8835b654ec4
Source dataset
uspto-grants-2005_07
Patent number
US06916921B2

Reaction notes

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