Triethylamine → HCID 86736874, compound

HRID 1701447Notes

Reaction equation

HRID 1701447 reaction equation
[OH:1][C@@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C@@H:17]([O:23][C:24](=[O:27])[CH2:25][I:26])[CH2:16][C@@:15]2([CH3:28])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[I:26][CH2:25][C:24]([O:23][C@H:17]1[CH2:16][C@@:15]2([CH3:28])[C@@H:8]([CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[C@H:7]2[C@H:18]1[C@:19]1([CH3:22])[C@@H:4]([CH2:5][CH2:6]2)[CH2:3][C@H:2]([O:1][S:37]([CH3:36])(=[O:39])=[O:38])[CH2:21][CH2:20]1)=[O:27]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 86736867HCID 86736867, compound

Product 1

HCID 86736874HCID 86736874, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 3α-hydroxy-11β-iodoacetoxy-5α-pregnan-20-one (20 g) in methylene chloride (400 ml) containing triethylamine (8.4 ml) was cooled to -5° and added dropwise with good stirring to a cooled (-5°) solution of methanesulphonyl chloride (3.77 ml) in methylene chloride (50 ml) at such a rate that the temperature did not exceed +1°. After 30 minutes a further portion of methanesulphonyl chloride (3 ml) and triethylamine (6 ml) was added in a small volume of methylene chloride. After 10 minutes the solution was washed with water, dried and evaporated to give a yellow solid (22.43 g). Crystallization of a small portion afforded an analytical sample of title compound, m.p. 142°-143°, [α]D +83.2°.

Workup

  1. temperaturewas cooled to -5°
  2. additionadded dropwise
  3. customdid not exceed +1°
  4. washAfter 10 minutes the solution was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-2e525752feb54e33b4c9a7a117a6be72
Source dataset
uspto-grants-1980_03
Patent number
US04192871

Reaction notes

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