Hydrochloric Acid → HCID 70479606, compound

HRID 615189Notes

Reaction equation

HRID 615189 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]C)=[O:28])[CH2:4][C@@H:3]1[OH:31].[ClH:32]>O1CCOCC1.O>[ClH:32].[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]([OH:29])=[O:28])[CH2:4][C@@H:3]1[OH:31]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 70479527HCID 70479527, compound

Product 1

HCID 70479606HCID 70479606, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Methyl 2β,3α-dihydroxy-11α-(3-methylbutylamino)5α-androstane-17β-carboxylate (750 mg) in dioxan (20 ml) was treated with concentrated hydrochloric acid (3 ml) and water (10 ml) and heated on a steam bath for 5 days. The cooled mixture was diluted with water (200 ml) and acidified to pH 1 with dilute hydrochloric acid and extracted with ethyl acetate (3×). The extracts were washed with brine, dried and evaporated to give a foam (426 mg). This was purified by preparative t.l.c. in chloroform/methanol (4:1) to give the title compound (146 mg), [α]D +17° (in dimethyl sulphoxide).

Workup

  1. temperatureheated on a steam bath for 5 days
  2. extractionextracted with ethyl acetate (3×)
  3. washThe extracts were washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-d729908d362f463ebe62f1d89d2af7b1
Source dataset
uspto-grants-1985_02
Patent number
US04497805

Reaction notes

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