Butanal → HCID 54204022, compound

HRID 1017998Notes

Reaction equation

HRID 1017998 reaction equation
[C:1]([O:5][C:6](=[O:39])[CH2:7][CH:8]([NH2:38])[C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:37])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[O:26])=[C:20]([O:35][CH3:36])[CH:19]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH:40](=O)[CH2:41][CH2:42][CH3:43].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+].Cl.C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6](=[O:39])[CH2:7][CH:8]([NH:38][CH2:40][CH2:41][CH2:42][CH3:43])[C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:37])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[O:26])=[C:20]([O:35][CH3:36])[CH:19]=2)=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 6

HCID 261ButanalHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 53940188HCID 53940188, compound

Product 1

HCID 54204022HCID 54204022, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-amino-3-(4-{3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetylamino}phenyl)-propanoic acid tert-butyl ester [53 mg, Reference Example 7(b)], butyraldehyde (14 mg), sodium acetate (16 mg) and 4 Å molecular sieves (0.2 g) in methanol (5 ml) was stirred at ambient temperature under an atmosphere of nitrogen and then treated with sodium cyanoborohydride (13 mg). After stirring for 1 hour the reaction mixture was treated dropwise with hydrochloric acid (0.5 ml, 1M) then poured into 10% aqueous potassium carbonate solution (10 ml). The mixture was extracted with ethyl acetate (30 ml). The organic phase was dried over magnesium sulphate and then evaporated. The residue was subjected to flash chromatography on silica gel eluting with ethyl acetate to give the title compound (44 mg) as a yellow foam.

Workup

  1. stirringAfter stirring for 1 hour the reaction mixture
  2. extractionThe mixture was extracted with ethyl acetate (30 ml)
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-202aff9d25b24f04bcfdf0867293708b
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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