Maleic Acid → HCID 12961957, compound

HRID 1065695Notes

Reaction equation

HRID 1065695 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH2:9][C@H:10]1[C@H:15]([OH:16])[CH2:14][C@H:13]2[C@H:17]3[C@H:27]([CH2:28][CH2:29][C@:11]12[CH3:12])[C@:25]1([CH3:26])[C@H:20]([CH2:21][C@@H:22]([OH:30])[CH2:23][CH2:24]1)[CH2:19][CH2:18]3>C(O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[NH2:9][C@H:10]1[C@H:15]([OH:16])[CH2:14][C@H:13]2[C@H:17]3[C@H:27]([CH2:28][CH2:29][C@:11]12[CH3:12])[C@:25]1([CH3:26])[C@H:20]([CH2:21][C@@H:22]([OH:30])[CH2:23][CH2:24]1)[CH2:19][CH2:18]3

Participants

4

Reactant 2

HCID 444266Maleic AcidHCID 12961956HCID 12961956, compound

Product 1

HCID 12961957HCID 12961957, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of maleic acid (2.5 g) in ethanol (25 ml) was added to a solution of 17β-amino-5α-androstane-3β,16α-diol (6.6 g) in ethanol (300 ml). Evaporation of the solvent and crystallisation of the residue from methanol-ethylacetate gave 17β-amino-5α-androstane-3β,16α-diol (Z)-2-butenedioate (1:1) (salt) as prisms (3.1 g), m.p. 193°-197° C., [α]D -9° (c, 0.9 in MeOH).

Workup

  1. customEvaporation of the solvent and crystallisation of the residue from methanol-ethylacetate

Sources & evidence

ORD record
ord-3bbde1b23454486a8d508013408050ab
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

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