Acetic Anhydride → HCID 10861689, compound

HRID 1736640Notes

Reaction equation

HRID 1736640 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14]([CH2:15][C@@H:16]([OH:24])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)([O:3][CH3:4])=[O:2].[C:25](OC(=O)C)(=[O:27])[CH3:26]>N1C=CC=CC=1>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14]([CH2:15][C@@H:16]([O:24][C:25](=[O:27])[CH3:26])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 25186817beta-Carbomethoxyandrost-5-en-3beta-ol

Product 1

HCID 10861689HCID 10861689, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mechanically stirred solution of 17β-carbomethoxy-3β-hydroxy-5-androstene (100 g, 0.30 mol), prepared as described in Rasmusson et al., Journal of Medicinal Chemistry 1984, 27, 1690, incorporated herein by reference, in pyridine (750 mL) in a 2 L 4-necked round bottom flask equipped with an addition funnel at ambient temperature is added acetic anhydride (130 mL, 1.38 mol). The resulting dark solution is stirred at ambient temperature for 18 h, transferred to an addition funnel, and added drop wise to 3 L of ice-water. The resulting precipitate is collected by filtration, washed with 2×1 L H2O, and dried under vacuum to afford 17β-carbomethoxy-3β-acetoxy-5-androstene; 1H NMR (400 MHz, CDCl3) δ5.36 (br d, J=5.1 Hz, 1H), 4.59 (m, 1H), 3.67 (s, 3H), 2.37-2.29 (m, 3H), 2.20-2.08 (m, 1H), 2.03 (s, 3H), 2.02-1.97 (m, 2H), 1.90-1.38 (m, 10H), 1.34-1.21 (m, 2H), 1.18-1.05 m, 2H), 1.02 (s, 3H), 1.00-0.96 (m, 1H), 0.66 (s, 3H).

Workup

  1. customequipped with an addition funnel at ambient temperature
  2. customtransferred to an addition funnel
  3. filtrationThe resulting precipitate is collected by filtration
  4. washwashed with 2×1 L H2O
  5. customdried under vacuum

Sources & evidence

ORD record
ord-cbda5530e5684dab9325387110561b95
Source dataset
uspto-grants-1996_07
Patent number
US05541322

Reaction notes

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