Maleic Acid → HCID 12962055, compound

HRID 1065702Notes

Reaction equation

HRID 1065702 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[OH:9][C@@H:10]1[CH2:15][C@H:14]2[C@H:16]3[C@H:26]([CH2:27][CH2:28][C@:12]2([CH3:13])[C@H:11]1[NH:30][CH3:31])[C@:24]1([CH3:25])[C:19](=[CH:20][C:21](=[O:29])[CH2:22][CH2:23]1)[CH2:18][CH2:17]3>C(O)C.ClCCl>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[OH:9][C@@H:10]1[CH2:15][C@H:14]2[C@H:16]3[C@H:26]([CH2:27][CH2:28][C@:12]2([CH3:13])[C@H:11]1[NH:30][CH3:31])[C@:24]1([CH3:25])[C:19](=[CH:20][C:21](=[O:29])[CH2:22][CH2:23]1)[CH2:18][CH2:17]3

Participants

5

Reactant 2

HCID 444266Maleic AcidHCID 12962056HCID 12962056, compound

Product 1

HCID 12962055HCID 12962055, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of maleic acid (0.73 g) in ethanol (15 ml) was added to a solution of 16α-hyroxy-17β-methylamino-androst-4-en-3-one (2 g) in dichloromethane (15 ml) and ethanol (15 ml). Evaporation of the solvent gave a solid residue which was crystallised from dichloromethane-acetone to give 16α-hydroxy-17β-methylamino-androst-4-en-3-one (Z)-2-butenedioate as prisms (2.65 g), m.p. 193° C. (decomp.), [α]D +114° (c 0.88 in EtOH).

Workup

  1. customEvaporation of the solvent
  2. customgave a solid residue which
  3. customwas crystallised from dichloromethane-acetone

Sources & evidence

ORD record
ord-169bc95f42404cf3b4109744c20372ab
Source dataset
uspto-grants-1982_05
Patent number
US04330539

Reaction notes

Loading…