Maleic Acid → HCID 12961952, compound

HRID 1065693Notes

Reaction equation

HRID 1065693 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH3:9][NH:10][C@H:11]1[C@@H:16]([OH:17])[CH2:15][C@H:14]2[C@H:18]3[C@H:28]([CH2:29][CH2:30][C@:12]12[CH3:13])[C@:26]1([CH3:27])[C@H:21]([CH2:22][C@@H:23]([OH:31])[CH2:24][CH2:25]1)[CH2:20][CH2:19]3>C(O)C.CO>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[CH3:9][NH:10][C@H:11]1[C@@H:16]([OH:17])[CH2:15][C@H:14]2[C@H:18]3[C@H:28]([CH2:29][CH2:30][C@:12]12[CH3:13])[C@:26]1([CH3:27])[C@H:21]([CH2:22][C@@H:23]([OH:31])[CH2:24][CH2:25]1)[CH2:20][CH2:19]3

Participants

5

Reactant 2

HCID 444266Maleic AcidHCID 12961951HCID 12961951, compound

Product 1

HCID 12961952HCID 12961952, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A solution of maleic acid (1.1 g) in ethanol (30 ml) was added to a solution of 17β-methylamino-5α-androstane-3β,16β-diol (3.05 g) in methanol (600 ml) and the solution was concentrated, treated with charcoal, and filtered. The filtrate was evaporated to give a froth (3.9 g), which crystallised from acetone to give 17β-methylamino-5α-androstane-3β,16β-diol (Z)-2-butenedioate (1:1) (salt) (3.19 g), m.p. 126°-129° C. and 184°-187° C., [α]D +21.2° (c 1.05 in MeOH).

Workup

  1. concentrationthe solution was concentrated
  2. additiontreated with charcoal
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customto give a froth (3.9 g), which
  6. customcrystallised from acetone

Sources & evidence

ORD record
ord-ddb4a51d524f4e3785c93d4138494fd7
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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