Water → HCID 86746639, compound

HRID 1613976Notes

Reaction equation

HRID 1613976 reaction equation
[CH2:1]1[CH2:31][O:30][C:3]2([CH2:25][CH2:24][C@@:23]3([CH3:26])[C:5](=[CH:6][CH2:7][C@@H:8]4[C@:22]3([OH:27])[CH2:21][CH2:20][C@@:19]3([CH3:28])[C@H:9]4[CH2:10][C@H:11]([CH3:29])[C:12]3=[C:13]([NH:16][CH:17]=[O:18])[CH2:14][OH:15])[CH2:4]2)[O:2]1.C(Cl)Cl.[OH2:35].N1[CH:41]=[CH:40]C=CC=1>C(OC(=O)C)(=O)C>[C:40]([O:15][CH2:14][C:13]([NH:16][CH:17]=[O:18])=[C:12]1[C@:19]2([CH3:28])[C@H:9]([C@H:8]3[C@:22]([OH:27])([CH2:21][CH2:20]2)[C@:23]2([CH3:26])[C:5]([CH2:4][C:3]4([O:2][CH2:1][CH2:31][O:30]4)[CH2:25][CH2:24]2)=[CH:6][CH2:7]3)[CH2:10][C@@H:11]1[CH3:29])(=[O:35])[CH3:41]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6344DichloromethaneHCID 86746640HCID 86746640, compound

Product 1

HCID 86746639HCID 86746639, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 3,3-ethylenedioxy-20-formamido-16β-methylpregna-5,17(20)-diene-9α,21-diol (80 mg) in pyridine (0.25 ml) and acetic anhydride (0.12 ml) was stirred at room temperature for 7 hours after which TLC indicated the conversion to be complete. Methylene chloride and water were added to the reaction mixture. The organic phase was washed with water to neutral pH, dried and concentrated under reduced pressure to afford 50 mg of the title compound as a mixture of the two rotamer forms of the 20-formamido group.

Workup

  1. washThe organic phase was washed with water to neutral pH
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-36b50dda9e32466090f187b9e06d5685
Source dataset
uspto-grants-1993_03
Patent number
US05194602

Reaction notes

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