Water → HCID 57282319, compound

HRID 1078278Notes

Reaction equation

HRID 1078278 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.[Br:33][C:34]1[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1.O>O1CCCC1>[Br:33][C:34]1[CH:39]=[CH:38][C:37]([S:40]([O:1][CH2:2][C:3](=[O:25])[C@@H:4]2[C@:21]3([CH3:22])[C@H:7]([C@H:8]4[C:18](=[CH:19][CH2:20]3)[C@:16]3([CH3:17])[C:11](=[CH:12][C:13](=[O:23])[CH:14]=[CH:15]3)[CH2:10][CH2:9]4)[CH2:6][C@H:5]2[CH3:24])(=[O:42])=[O:41])=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 1458523921-Hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione

Product 1

HCID 57282319HCID 57282319, 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. 13.1 g (51.4 mmoles) of 4-bromobenzenesulfonyl chloride are added to the above solution and the reaction mixture is stirred at room temperature for 4 hours, then dropwise added to 450 ml of water while stirring. The precipitate is filtered off, dried and recrystallized from ether to give the title compound in a yield of 11.0 g (67.07%), m.p.:124°-129° 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-86bbac541b274cd7a73c7407f3437359
Source dataset
uspto-grants-1996_08
Patent number
US05547949

Reaction notes

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