Benzoyl chloride → (20S)-21-hydroxy-20-methylpregn-4-en-3-one benzoate

HRID 1587565Notes

Reaction equation

HRID 1587565 reaction equation
[OH:1][CH2:2][C@@H:3]([CH3:24])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.C(N(CC)CC)C.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>ClCCl>[C:32]([OH:39])(=[O:1])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[OH:1][CH2:2][C@@H:3]([CH3:24])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 11142115HCID 11142115, compound

Product 1

HCID 86745920(20S)-21-hydroxy-20-methylpregn-4-en-3-one benzoateYield 171.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (20S)-21-hydroxy-20-methylpregn-4-en-3-one (8.0 g, 24.2 mmole) in dichloromethane (200 mL) was cooled in an ice-water bath and treated sequentially with triethylamine (3.69 mL, 26.6 mmole) and benzoyl chloride (3.09 mL, 26.6 mmole) and stirred for 16 hours at room temperature. After the reaction mixture was diluted with dichloromethane (200 mL), it was extracted with ether, dried over magnesium sulfate and filtered and the filtrate was concentrated to a solid which was purified by flash chromatography to give (20S)-21-hydroxy-20-methylpregn-4-en-3-one benzoate (9.4 g, 89.5%) melting at 193°-195° C. after recrystallization from acetone. IR 1716, 1676, 1614 (m), 1284 cm-1 ; MS (CI) 435 (100%, M+1), 313 (70%, M+1-PhCOOH); 1H NMR (CDCl3) δ 0.77 (3H, s, C18 -Me), 1.04 (d, C 22 -Me), 1.19 (s, C19 -Me), 4.05 (1H, dd, 1/2 C21 -CH2), 4.34 (1H, dd, 1/2 C21 -CH2), 5.72 (1H, s, C4 -H), 7.45 (2H, t), 7.56 (1H, t), 8.04 (2H, dd).

Workup

  1. extractionwas extracted with ether
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to a solid which
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-898e5957ce754fd69c2cfa76034c875c
Source dataset
uspto-grants-1993_06
Patent number
US05218110

Reaction notes

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