Acetic Acid → HCID 9929531, compound

HRID 1290304Notes

Reaction equation

HRID 1290304 reaction equation
CC(C)([O-])C.[K+].[OH:7][CH2:8][C@H:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[CH3:10].C([O:35][N+:36]([O-])=[O:37])C(C)C.C(O)(=O)C>C(O)(C)(C)C.ClCCl>[OH:7][CH2:8][C@H:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[C:19]([N+:36]([O-:37])=[O:35])[C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[CH3:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 10974Isobutyl nitrateHCID 11142115HCID 11142115, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 9929531HCID 9929531, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

Potassium tert-butoxide (7.6 g, 67.8 mM), (20S)-20-hydroxymethylpregn-4-en-3-one (6.6 g, 20 mM) in tert-butanol is heated at reflux temperature for 60 minutes under an argon atmosphere. Isobutylnitrate (2.34 ml, 20 mM) is then added in one continuous portion. After 20 minutes of further refluxing, the reaction vessel is cooled to room temperature. Acetic acid (10 ml) is then added, and the reaction vessel stirred for 18 hours, after which the combination is diluted with dichloromethane (200 mL). The solids are removed, washed, and recombined with the washing residue and subsequently purified as described in Example 1 to give crystallized (20S)-20-hydroxymethyl-4-nitropregn-4-en-3-one.

Workup

  1. temperatureat reflux temperature for 60 minutes under an argon atmosphere
  2. customThe solids are removed
  3. washwashed
  4. customsubsequently purified
  5. customto give
  6. customcrystallized (20S)-20-hydroxymethyl-4-nitropregn-4-en-3-one

Sources & evidence

ORD record
ord-af4e2c58ce77416b821731c998f42c80
Source dataset
uspto-grants-1998_05
Patent number
US05750744

Reaction notes

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