Acetic Acid → HCID 67726335, compound

HRID 1492337Notes

Reaction equation

HRID 1492337 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[CH3:13][C@:14]12[CH2:30][CH2:29][C@H:28]3[C@@H:19]([CH2:20][CH2:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=43)[C@@H:18]1[CH2:17][CH2:16][C:15]2=O.C1COCC1>CO>[CH2:1]([NH:8][C@H:15]1[CH2:16][CH2:17][C@H:18]2[C@H:19]3[C@H:28]([CH2:29][CH2:30][C@:14]12[CH3:13])[C:27]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:21][CH2:20]3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 58823-Deoxy-estroneHCID 7504BenzylamineHCID 8028Tetrahydrofuran

Product 1

HCID 67726335HCID 67726335, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzylamine (11.2 ml) in dry methanol (75 ml) was added sequentially acetic acid (6.16 ml), estra-1,3,5(10)-trien-17-one (5.21 g) sodium cyanoborohydride (1.35 g), and THF (60 ml) under a N2 atmosphere. The resulting mixture was stirred overnight at room temperature, concentrated in vacuo, diluted with water (200 ml), and made alkaline with aqueous sodium hydroxide (50 ml). The suspension was extracted with ethyl acetate (3×200 ml) and the combined extracts were dried over MgSO4, filtered and concentrated to an oil. This product was chromatographed (300 g silica gel 0.4-4-96 Et3N-acetone-hexane, 20 ml fractions) and gave impure product in fractions 53-79 and pure product in fractions 80-135. The latter were combined and after removal of the solvent gave the title compound as crystals, mp 71°-74° C. (PLA2, diabetes)

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water (200 ml)
  3. extractionThe suspension was extracted with ethyl acetate (3×200 ml)
  4. dry with materialthe combined extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to an oil
  7. customThis product was chromatographed (300 g silica gel 0.4-4-96 Et3N-acetone-hexane, 20 ml fractions)
  8. customgave impure product in fractions 53-79 and pure product in fractions 80-135
  9. customafter removal of the solvent

Sources & evidence

ORD record
ord-5a0ca1cdd4124399a2984f221faf50b3
Source dataset
uspto-grants-1994_12
Patent number
US05373095

Reaction notes

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