Acetic Acid → HCID 10740469, compound

HRID 1872084Notes

Reaction equation

HRID 1872084 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[C:12]1[C:13]([S:18]([NH:21][C:22]2[O:26][N:25]=[C:24]([CH3:27])[C:23]=2[CH3:28])(=[O:20])=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1.[C:29]([O-])(=O)C.[Na+].C(O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO>[CH3:29][NH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:5]=[CH:4][C:3]=1[C:12]1[C:13]([S:18]([NH:21][C:22]2[O:26][N:25]=[C:24]([CH3:27])[C:23]=2[CH3:28])(=[O:20])=[O:19])=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 9908909153624-15-8

Product 1

HCID 10740469HCID 10740469, compoundYield 16.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound of Example 46 (135 mg, 0.34 mmol), sodium acetate (28 mg, 0.34 mmol) and acetic acid (41 mg, 0.68 mmol) in methanol (3.4 mL), formaldehyde (37% in water, 0.033 mL, 0.41 mmol) and sodium cyanoborohydride (21 mg, 0.34 mmol) were added. The mixture was stirred for 1 hour, concentrated, diluted with ethyl acetate and washed with water and brine, dred and concentrated. The residue was subjected to preparative HPLC on a 30×500 mm ODS S10 column using 56% methanol, 44% water and 0.1% trifluoroacetic acid to provide 23 mg of the title compound (16%) as a white solid, m.p. 125-128° C., as well as 30 mg of the title compound of Example 50 (20%) as a light yellow solid, m.p. 127-129° C.

Workup

  1. concentrationconcentrated
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dda6e2f96d4145a58b1ddf50bbbae6c8
Source dataset
uspto-grants-2000_08
Patent number
US06107320

Reaction notes

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