Acetic Acid → HCID 22730010, compound

HRID 2356120Notes

Reaction equation

HRID 2356120 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-b0aa2f2792dd47e38f83b47d92aae46b
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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