Benzaldehyde, 4-(phenylmethoxy)- → HCID 54470705, compound

HRID 380175Notes

Reaction equation

HRID 380175 reaction equation
Cl.[C:2]([O:6][C:7](=[O:10])[CH2:8][NH2:9])([CH3:5])([CH3:4])[CH3:3].[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:2]([O:6][C:7](=[O:10])[CH2:8][NH:9][CH2:23][C:22]1[CH:25]=[CH:26][C:19]([O:18][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:20][CH:21]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 516892Sodium BicarbonateHCID 2725036Glycine tert-butyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 54470705HCID 54470705, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of glycine t-butyl ester hydrochloride (0.84 g, 5 mmol), and 4-benzyloxy-benzaldehyde (0.53 g, 2.5 mmol) in CH2Cl2 (25 mL) at 0° C. was added sodium triacetoxyborohydride (0.81 g, 3.8 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 0.38 g (59%) of the title compound as a white solid.

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-e2a1e640911c4bc294ef3042e5f1f557
Source dataset
uspto-grants-2001_10
Patent number
US06300501B1

Reaction notes

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