Water → HCID 131710149, compound

HRID 1606371Notes

Reaction equation

HRID 1606371 reaction equation
[CH2:1]([O:3][C@H:4]1[CH2:23][C@@:22]2([CH3:24])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[C:20](=[O:25])[CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6][C@@H:5]1[O:27][C:28](=[O:31])[CH2:29]I)[CH3:2].[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33].O>C(Cl)Cl>[CH2:32]([N:34]([CH2:29][C:28]([O:27][C@@H:5]1[C@@H:4]([O:3][CH2:1][CH3:2])[CH2:23][C@@:22]2([CH3:24])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:21]2[C:20](=[O:25])[CH2:19][C@@:18]2([CH3:26])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C:15](=[O:17])[CH3:16])[CH2:6]1)=[O:31])[CH2:35][CH3:36])[CH3:33]

Participants

5

Reactant 3

HCID 962WaterHCID 8021DiethylamineHCID 86733304HCID 86733304, compound

Product 1

HCID 131710149HCID 131710149, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2β-Ethoxy-3α-iodoacetoxy-5α-pregnane-11,20-dione (460 mg) was dissolved in methylene chloride (25 ml) and diethylamine (1 ml) added to the solution. The mixture was stirred at room temperature for one-half hour. The mixture was poured into water and the organic layer washed with water (100 ml.), dried over anhydrous sodium sulphate and evaporated to a red oil (410 mg.) which was purified by preparative T.L.C. using ethyl acetate/petrol (2/1) run twice. The main band (RF 0.4) gave title compound (230 mg) as a pale yellow oil [α]D + 100° (c = 0.9).

Workup

  1. washthe organic layer washed with water (100 ml.)
  2. dry with materialdried over anhydrous sodium sulphate
  3. customevaporated to a red oil (410 mg.) which
  4. customwas purified by preparative T.L.C

Sources & evidence

ORD record
ord-a1ca6c181a0c41d9ad6fe82deed68972
Source dataset
uspto-grants-1976_04
Patent number
US03952031

Reaction notes

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