Sulfuric Acid → HCID 70479527, compound

HRID 615195Notes

Reaction equation

HRID 615195 reaction equation
[OH:1][C@H:2]1[CH2:19][C@@:18]2([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[C@H:16]([NH:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:27]([O:29][CH2:30]CC)=[O:28])[CH2:4][C@@H:3]1[OH:33].S(=O)(=O)(O)O>CO>[OH:1][C@H:2]1[CH2:19][C@@:18]2([CH3:20])[C@@H:5]([CH2:6][CH2:7][C@@H:8]3[C@@H:17]2[C@H:16]([NH:21][CH2:22][CH2:23][CH:24]([CH3:26])[CH3:25])[CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C@@H:12]2[C:27]([O:29][CH3:30])=[O:28])[CH2:4][C@@H:3]1[OH:33]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 70479025HCID 70479025, compound

Product 1

HCID 70479527HCID 70479527, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of propyl 2β,3α-dihydroxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate (100 mg) in methanol (10 ml) was heated at 100° C. with concentrated sulphuric acid (0.2 ml) for 48 h. The cooled mixture was evaporated, the residue brought to pH 10 by the addition of 0.88 ammonia solution and extracted with ethyl acetate (3×). The extracts were washed with water, dried and evaporated to give the title compound (80 mg), [α]D +22.4°.

Workup

  1. customThe cooled mixture was evaporated
  2. additionthe residue brought to pH 10 by the addition of 0.88 ammonia solution
  3. extractionextracted with ethyl acetate (3×)
  4. washThe extracts were washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-da4083fbc89e40d9adc8e6e929b03a43
Source dataset
uspto-grants-1985_02
Patent number
US04497805

Reaction notes

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