Water → HCID 57078569, compound

HRID 1078279Notes

Reaction equation

HRID 1078279 reaction equation
[OH:1][CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C:18](=[CH:19][CH2:20]2)[C@:16]2([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][C@H:5]1[CH3:24].C(N(CC)CC)C.[N+:33]([C:36]1[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1)([O-:35])=[O:34].O>O1CCCC1>[CH3:24][C@@H:5]1[CH2:6][C@@H:7]2[C@:21]([CH3:22])([CH2:20][CH:19]=[C:18]3[C@H:8]2[CH2:9][CH2:10][C:11]2[C@:16]3([CH3:17])[CH:15]=[CH:14][C:13](=[O:23])[CH:12]=2)[C@H:4]1[C:3](=[O:25])[CH2:2][O:1][S:42]([C:39]1[CH:38]=[CH:37][C:36]([N+:33]([O-:35])=[O:34])=[CH:41][CH:40]=1)(=[O:43])=[O:44]

Participants

6

Reactant 4

HCID 962WaterHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 1458523921-Hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione

Product 1

HCID 57078569HCID 57078569, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 10.0 g (29.4 mmoles) of 21-hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione in 100 ml of tetrahydrofuran, 7.14 ml (51.4 mmoles) of triethylamine, then at 0° C. 11.4 g (51.4 mmoles) of 4-nitrobenzenesulfonyl chloride are added to the above solution. Subsequently, the reaction mixture is stirred at room temperature for 2 hours, then dropwise added to 450 ml of water while stirring. The precipitate is filtered off, dried and recrystallized from ether to obtain the title compound in a yield of 13.5 g (87.66%), m.p.:151°-160° C.

Workup

  1. customat 0° C
  2. stirringwhile stirring
  3. filtrationThe precipitate is filtered off
  4. customdried
  5. customrecrystallized from ether

Sources & evidence

ORD record
ord-65d4c7425254486e95e877ced029daf4
Source dataset
uspto-grants-1996_08
Patent number
US05547949

Reaction notes

Loading…