6-Aminopenicillanic acid → Nandrolone

HRID 2304363Notes

Reaction equation

HRID 2304363 reaction equation
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@H:20]([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.C1(C(C([O-])=O)C([O-])=O)C=CC=CC=1.CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O.C(N1C=CN=C1)(N1C=CN=C1)=O>>[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@H:20]([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3

Participants

4

Reactant 3

HCID 110826-Aminopenicillanic acidHCID 682631,1'-CarbonyldiimidazoleHCID 86758457HCID 86758457, compound

Product 1

HCID 9904Nandrolone

Procedure

The coupling of the nandrolone phenylmalonate to 6-APA is carried out conventionally after activation with carbonyldiimidazole (CDI). The purification of the conjugate is obtained by extraction in ether in a medium of pH 2 and 8.5 before final recrystallization from a toluene-white petrolatum mixture (see Table 9).

Workup

  1. customThe purification of the conjugate
  2. customis obtained by extraction in ether in a medium of pH 2 and 8.5 before final
  3. customrecrystallization from a toluene-white petrolatum mixture (see Table 9)

Sources & evidence

ORD record
ord-b62ca34af692495fb188b389a1a4e67a
Source dataset
uspto-grants-2002_08
Patent number
US06436649B1

Reaction notes

Loading…