Water → HCID 18507128, compound

HRID 1633545Notes

Reaction equation

HRID 1633545 reaction equation
[NH2:1][CH2:2][C:3]([C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)[OH:4].C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=[O:30].O>C1(C)C=CC=CC=1.CCOC(C)=O>[Br:19][C:16]1[CH:15]=[CH:14][C:13]([C:3]([OH:4])([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=2)[CH2:2][NH:1][C:29](=[O:30])[CH2:28][Cl:27])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 18507133HCID 18507133, compound

Product 1

HCID 18507128HCID 18507128, compoundYield 92.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-1-(4-bromo-phenyl)-1-(3-methoxy-phenyl)-ethanol (0.94 g, 2.92 mmol) in toluene (10 mL) at 0° C. was added triethylamine (0.41 mL, 3.07 mmol). To the reaction mixture was added a solution of chloroacetylchloride (0.23 mL, 2.92 mmol) in toluene (1 mL) and the reaction was stirred at 0° C. for 30 min. and at room temperature for 1 h. To the reaction was added cold water (10 mL) and the mixture was stirred for 10 min. EtOAc was added (20 mL) and the layers were separated. The aqueous layer was washed with EtOAc (2×20 mL) and the combined organic extracts were dried over MgSO4, and concentrated. Purification by flash chromatography with hexanes/EtOAc (4:1) afforded 1.08 g of N-[2-(4-bromo-phenyl)-2-hydroxy-2-(3-methoxy-phenyl)-ethyl]-2-chloro-acetamide. 1HNMR (400 MHz, CDCl3) δ 7.45-7.41 (comp, 2H), 7.29-7.20 (comp, 3H), 6.97-6.96 (m, 1H), 6.93-6.90 (m, 1H), 6.86-6.85 (m, 1H), 6.85-6.79 (m, 1H), 4.14-3.98 (comp, 2H), 3.95 (s, 2H), 3.77 (s, 3H), MS (M+1) 380.0, 382.0.

Workup

  1. stirringthe mixture was stirred for 10 min
  2. customthe layers were separated
  3. washThe aqueous layer was washed with EtOAc (2×20 mL)
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customPurification by flash chromatography with hexanes/EtOAc (4:1)

Sources & evidence

ORD record
ord-9b76738bdf6146a5870668455d426787
Source dataset
uspto-grants-2003_01
Patent number
US06503905B1

Reaction notes

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