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Acetic Acid → HCID 67726335, compound

HRID 2082249
Notes
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Reaction equation

HRID 2082249 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 58823-DeoxyestroneHCID 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-7a84c3c59da3445aa586a662243f06fe
Source dataset
uspto-grants-1993_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05187299

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes