Sulfuric Acid → HCID 70479667, compound

HRID 615196Notes

Reaction equation

HRID 615196 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][CH3:30])=[O:28])[CH2:4][C@@H:3]1[OH:31].OS(O)(=O)=O>C1(O)CCCCC1>[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][CH:30]2[CH2:18][CH2:19][CH2:2][CH2:3][CH2:4]2)=[O:28])[CH2:4][C@@H:3]1[OH:31]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 70479527HCID 70479527, compound

Product 1

HCID 70479667HCID 70479667, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 7966CyclohexanolSolvent

Procedure

Methyl 2β,3α-dihydroxy-11α-(3-methylbutylamino)-5α-androstane-17β-carboxylate (410 mg) in cyclohexanol (2.5 ml) was heated at 100° C. with concentrated H2SO4 (0.2 ml) for 24 h. The cooled mixture was concentrated by evaporation and the residue purified by column chromatography using ethyl acetate/ammonia 50:1 to give an oil (194 mg). This was purified further by preparative t.l.c. in ethyl acetate/ammonia 50:1 to give the title compound (40 mg), [α]D +17°, νmax 1725 cm-1.

Workup

  1. concentrationThe cooled mixture was concentrated by evaporation
  2. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-6ef0cd8f69014683a33c5cd80d9e670f
Source dataset
uspto-grants-1985_02
Patent number
US04497805

Reaction notes

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