Propionic anhydride → HCID 70146704, compound

HRID 840181Notes

Reaction equation

HRID 840181 reaction equation
[CH:1]1([O:4][C@H:5]2[CH2:10][CH2:9][C@H:8]3[C@H:11]4[C@H:21]([CH2:22][CH2:23][C@:6]23[CH3:7])[C@:19]2([CH3:20])[C:14]([NH:15][C:16](=[O:24])[CH2:17][CH2:18]2)=[CH:13][C@@H:12]4O)[CH2:3][CH2:2]1.[C:26]([O:30][C:31](=O)[CH2:32][CH3:33])(=[O:29])CC>N1C=CC=CC=1.C(Cl)Cl>[CH:1]1([O:4][C@H:5]2[CH2:10][CH2:9][C@H:8]3[C@H:11]4[C@H:21]([CH2:22][CH2:23][C@:6]23[CH3:7])[C@:19]2([CH3:20])[C:14]([NH:15][C:16](=[O:24])[CH2:17][CH2:18]2)=[CH:13][C@@H:12]4[C:26]([O:30][CH2:31][CH2:32][CH3:33])=[O:29])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 31263Propionic anhydrideHCID 70146745HCID 70146745, compound

Product 1

HCID 70146704HCID 70146704, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

In a manner analogous to the procedure reported in Baer, H. et al., Can. J. Chem 1991, 69, 1563-1574, 17β-cyclopropyloxy-7β-hydroxy-4-aza-androst-5-en-3-one (1.000 g, 2.895 mmol) from Example 20A or otherwise obtained is dissolved in pyridine (20 mL). Proprionic anhydride (20.0 mL, 156.0 mmol) is added, and the mixture is stirred at room temperature under nitrogen for 12 hours. At the end of the reaction time, the solution is diluted with CH2Cl2 (150 mL) and washed with water (2×100 mL), saturated aqueous NaHCO3 (2×100 mL), water (100 mL) and brine (100 mL). The organic phase is then dried over MgSO4, filtered and evaporated to dryness. The residue is purified by flash chromatography (1:1 EtOAc/CH2Cl2) to give the title compound.

Workup

  1. washwashed with water (2×100 mL), saturated aqueous NaHCO3 (2×100 mL), water (100 mL) and brine (100 mL)
  2. dry with materialThe organic phase is then dried over MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue is purified by flash chromatography (1:1 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-ef3776c5bd4b4b8f9a989c5d767d2c58
Source dataset
uspto-grants-2002_04
Patent number
US06365597B1

Reaction notes

Loading…