Benzaldehyde, 4-(phenylmethoxy)- → HCID 10827000, compound

HRID 380179Notes

Reaction equation

HRID 380179 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].[CH2:8]([O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH:6][CH2:20][C:19]1[CH:22]=[CH:23][C:16]([O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 122755Glycine methyl ester hydrochlorideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 10827000HCID 10827000, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of glycine methyl ester hydrochloride (2.07 g, 16.5 mmol), and 4-benzyloxy-benzaldehyde (3.18 g, 15 mmol) in CH2Cl2 (50 mL) at 0° C. was added sodium triacetoxyborohydride (3.81 g, 18 mmol). The mixture was allowed to warm to room temperature and stirred overnight. Aqueous NaHCO3 was added, and the mixture was stirred for 30 minutes. The aqueous layer was extracted 3 times with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated. Flash chromatography (ethyl acetate) gave 1.98 g (46%) of the title compound as a white solid; mp 57-58° C.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionThe aqueous layer was extracted 3 times with CH2Cl2
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ed93d29928d04e9aa90199d387379f1c
Source dataset
uspto-grants-2001_10
Patent number
US06300501B1

Reaction notes

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