Formic Acid → HCID 86745914, compound

HRID 893032Notes

Reaction equation

HRID 893032 reaction equation
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][C:12]1[C:29](=[O:30])[CH2:28][CH2:27][C@@:26]2([CH3:31])[C:13]=1[CH2:14][CH2:15][C@@H:16]1[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]1[CH2:18][CH2:19][C@@H:20]2[C:32]([NH:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>O1CCCC1.O>[CH:1]([NH:11][C:12]1[C:29](=[O:30])[CH2:28][CH2:27][C@@:26]2([CH3:31])[C:13]=1[CH2:14][CH2:15][C@@H:16]1[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]1[CH2:18][CH2:19][C@@H:20]2[C:32]([NH:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[O:2]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 15281055HCID 15281055, compound

Product 1

HCID 86745914HCID 86745914, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of formic acid (0.22 mL, 5.84 mmole) and acetic anhydride (0.46 mL, 4.76 mmole) is heated at reflux temperature for 2 hours under a nitrogen atmosphere. The cooled solution is diluted with tetrahydrofuran (5 mL) and a solution of 4-amino-N-(1,1-dimethylethyl)-3-oxoandrost-4-ene-17β-carboxamide, (0.35 g, 0.91 mmole) in tetra-hydrofuran (10 mL) is added. The reaction is stirred overnight at room temperature and then diluted with water (25 mL). A gummy material separated which is extracted into diethyl ether-dichloromethane and washed with saturated aqueous sodium bicarbonate. The dried solution is concentrated to a yellow foam which is purified by flash chromatography (hexane-50% ethyl acetate then ethyl acetate) to give 4-formamido-N-(1,1-dimethylethyl)-3-oxoandrost-4-ene-17β-carboxamide (0.25 g, 67.6%, diethyl ether).

Workup

  1. temperatureat reflux temperature for 2 hours under a nitrogen atmosphere
  2. customA gummy material separated which
  3. extractionis extracted into diethyl ether-dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate
  5. concentrationThe dried solution is concentrated to a yellow foam which
  6. customis purified by flash chromatography (hexane-50% ethyl acetate

Sources & evidence

ORD record
ord-68db30b98db94d2795557f4557773118
Source dataset
uspto-grants-1992_06
Patent number
US05120840

Reaction notes

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