Acetic Acid → HCID 57842604, compound

HRID 735711Notes

Reaction equation

HRID 735711 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:13])[CH2:11][NH2:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH:12][CH2:11][C:10]([O:9][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[O:13])=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 707414-BromobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 11701227Benzyl 2-aminoacetate hydrochloride

Product 1

HCID 57842604HCID 57842604, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of glycine benzyl ester hydrochloride (2.02 g, 10.0 mmol) and 4-bromobenzaldehyde (1.85 g, 10.0 mmol) in 50 mL DCE, was added acetic acid (2.9 mL, 50 mmol) and TEA (1.4 mL, 10.0 mmol) to give a clear solution. Sodium triacetoxyborohydride (4.24 g, 20.0 mmol) was added. The suspension was stirred at rt for 17 h. The mixture was neutralized with sat. NaHCO3 and extracted with CH2Cl2 (3×). The combined organic extract washed with brine, dried (Na2SO4) and concentrated. The crude product was purified via flash chromatography (0 to 100% EtOAc in hexanes) to afford 80A (2.13 g, 64%). MS (ESI) m/z 334.0 (M+H)+.

Workup

  1. customto give a clear solution
  2. extractionextracted with CH2Cl2 (3×)
  3. extractionThe combined organic extract
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified via flash chromatography (0 to 100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6a7c1ef4fd9f4ebc8676d43c6b5b7c29
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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