Benzaldehyde → HCID 53825859, compound

HRID 1857550Notes

Reaction equation

HRID 1857550 reaction equation
[CH3:1][O:2][P:3]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH2:35])[CH:30]=1)([CH2:5][CH:6]([C:11](=[O:27])[NH:12][CH:13]([C:23](=[O:26])[NH:24][CH3:25])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4].[CH:36](=O)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[CH3:1][O:2][P:3]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([NH:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:30]=1)([CH2:5][CH:6]([C:11](=[O:27])[NH:12][CH:13]([C:23](=[O:26])[NH:24][CH3:25])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4]

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 53658361HCID 53658361, compound

Product 1

HCID 53825859HCID 53825859, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

(3-Aminobenzyl){2-[2-(4-methoxyphenyl)-1-methylcarbamoyl ethylcarbamoyl]-4-methylpentyl}phosphinic acid methyl ester (prepared as described in Example 4/Step A) (150 mg, 0.30 mmole), benzaldehyde (38 mg, 0.36 mmole), sodium cyanoborohydride (23 mg, 0.357 mmole) and acetic acid (1 drop) in methanol were stirred at room temperature for 3 hours. The reaction was quenched with 1N hydrochloric acid (few ml's) and the reaction mixture concentrated. The residue was dissolved in ethyl acetate (20 ml) and washed with 1N hydrochloric acid (20 ml), saturated sodium bicarbonate solution (20 ml) and dried with magnesium sulfate. Filtration and concentration gave the crude product which was purified by chromatography (3:97--methanol:methylene chloride) yielding 133 mg (75%) of (3-Benzylamino benzyl)-{2-[2-(4-methoxyphenyl)-1-methylcarbamoylethylcarbamoyl]-4-methylpentyl}phosphinic acid methyl ester as an oil.

Workup

  1. customwere stirred at room temperature for 3 hours
  2. customThe reaction was quenched with 1N hydrochloric acid (few ml's)
  3. concentrationthe reaction mixture concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate (20 ml)
  5. washwashed with 1N hydrochloric acid (20 ml), saturated sodium bicarbonate solution (20 ml)
  6. dry with materialdried with magnesium sulfate
  7. filtrationFiltration and concentration
  8. customgave the crude product which
  9. customwas purified by chromatography (3:97--methanol:methylene chloride)

Sources & evidence

ORD record
ord-cf6a9ff2b9c44376bc8696fd7dfadd7d
Source dataset
uspto-grants-2000_11
Patent number
US06147061

Reaction notes

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