Water → HCID 14307792, compound

HRID 1109927Notes

Reaction equation

HRID 1109927 reaction equation
[OH:1][C@:2]1([C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C:25](=[CH: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)[C:3](=[O:11])[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[Cl:31][C:32]1[CH:33]=[C:34]([N:38]=[C:39]=[O:40])[CH:35]=[CH:36][CH:37]=1.O>CN(C=O)C>[OH:1][C@:2]1([C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C:25](=[CH: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)[C:3](=[O:11])[CH2:4][N:5]1[CH2:6][CH2:7][N:8]([C:39]([NH:38][C:34]2[CH:35]=[CH:36][CH:37]=[C:32]([Cl:31])[CH:33]=2)=[O:40])[CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 962WaterHCID 17968Benzene, 1-chloro-3-isocyanato-HCID 14654949HCID 14654949, compound

Product 1

HCID 14307792HCID 14307792, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

17α-Hydroxy-21-(1-piperazinyl)pregna-4,9(11)-diene-3,20-dione (EXAMPLE 6A, 5.00 g) is treated in DMF (20 ml) with m-chlorophenylisocyanate (1.84 g) for 3 days. The mixture is poured into water (200 ml). After 1 hr, the liquid is decanted. The solid is dissolved in methylene chloride and is extracted with aqueous sodium bicarbonate. The phases are separated and the organic phase is dried over sodium sulfate and concentrated. The concentrate is chromatographed on silica gel (3% methanol in methylene chloride to 4%) to give the title compound which is crystallized from hot ethyl acetate.

Workup

  1. customthe liquid is decanted
  2. dissolutionThe solid is dissolved in methylene chloride
  3. extractionis extracted with aqueous sodium bicarbonate
  4. customThe phases are separated
  5. dry with materialthe organic phase is dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe concentrate is chromatographed on silica gel (3% methanol in methylene chloride to 4%)

Sources & evidence

ORD record
ord-ccdb8219968b48b4be4992094cfab6d5
Source dataset
uspto-grants-1994_06
Patent number
US05322943

Reaction notes

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