Acetic Acid → HCID 22730010, compound

HRID 2085786Notes

Reaction equation

HRID 2085786 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=2)=[C:5]([O:19][CH3:20])[CH:4]=1)=O.[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C([BH3-])#N.[Na+].C(O)(=O)C>C1COCC1.CO.C(OCC)(=O)C>[CH3:20][O:19][C:5]1[CH:4]=[C:3]([CH2:1][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:8]=[CH:7][C:6]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 11558086Methyl 4'-formyl-2'-methoxy[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 22730010HCID 22730010, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 122I (135 mg, 0.50 mmol), morpholine (100 mg), 1M sodium cyanoborohydride in THF (1 mL) in methanol (2 mL) and acetic acid (0.3 mL) was stirred for 18 hours, diluted with ethyl acetate (100 mL), washed sequentially with 2M sodium carbonate (10 mL), water (20 mL), and brine (10 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 30-100% ethyl acetate/hexanes to provide the desired product. MS (DCI(+)) m/e 342 (M+H)+.

Workup

  1. washwashed sequentially with 2M sodium carbonate (10 mL), water (20 mL), and brine (10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash column chromatography on silica gel with 30-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-05ea6e9fe2f147578a0fce98b748e8c6
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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