Methanol → HCID 70582853, compound

HRID 1701490Notes

Reaction equation

HRID 1701490 reaction equation
[OH:1][C@@H:2]1[C@@:24]2([CH3:25])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:26])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@@H:14]([CH3:19])[CH2:15][C:16]([OH:18])=[O:17])[CH2:5][C@@H:4]([OH:27])[CH2:3]1.CO.[N+](=[CH2:32])=[N-]>C(O)(=O)C>[CH3:32][O:17][C:16]([CH2:15][C@H:14]([CH3:19])[C@@H:13]1[C@:20]2([CH3:26])[C@H:10]([C@H:9]3[C@H:23]([CH2:22][CH2:21]2)[C@:24]2([CH3:25])[C:6]([CH2:5][C@@H:4]([OH:27])[CH2:3][C@@H:2]2[OH:1])=[CH:7][CH2:8]3)[CH2:11][CH2:12]1)=[O:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 9550DiazomethaneHCID 57284080HCID 57284080, compound

Product 1

HCID 70582853HCID 70582853, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1.0 g of (20S)-1α,3β-dihydroxy-20-methyl-pregn-5-ene-21-carboxylic acid in 50 ml. of methanol was treated with an ethereal solution containing 4 mmol of diazomethane and stored at room temperature for 30 minutes. After addition of glacial acetic acid, the mixture was concentrated in vacuo. The crystalline residue, which was uniform according to thin-layer chromatography, was recrystallised from concentrated methanolic solution to give 0.79 g of (20S)-1α,3β-dihydroxy-20-methyl-pregn-5-ene-21-carboxylic acid methyl ester in the form of colourless prisms of melting point 144°-146° C.; [α]D =-56° (c=0.5 in chloroform). Each mol of this ester contained 1 mol of methanol of crystallisation. EXAMPLE 16

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customwas recrystallised from concentrated methanolic solution

Sources & evidence

ORD record
ord-a5eaaaaabcba4955bec41130e0a9959c
Source dataset
uspto-grants-1980_03
Patent number
US04193921

Reaction notes

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