Ethyl bromoacetate → HCID 15870967, compound

HRID 2304592Notes

Reaction equation

HRID 2304592 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:23](=[O:25])[CH3:24])(=[O:21])=[O:20])=[CH:15][CH:14]=1.Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].CCN(CC)CC>ClCCl>[C:23]([N:22]([S:19]([C:16]1[CH:17]=[CH:18][C:13]([C:3]2[C:4]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)=[N:5][O:6][C:2]=2[CH3:1])=[CH:14][CH:15]=1)(=[O:20])=[O:21])[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetate2×HCID 8471Triethylamine2×HCID 10833494N-((4-(5-Methyl-3-phenylisoxazol-4-yl)phenyl)sulfonyl)acetamide

Product 1

HCID 15870967HCID 15870967, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of N-[[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl]acetamide (Example 39) (0.612 g, 1.72 mmol) in dichloromethane was treated with ethyl bromoacetate (0.20 mL, 0.29 g, 1.72 mmol) and Et3N (0.26 mL, 0.19 g, 1.89 mmol). After 7 days the reaction was still incomplete by TLC. Additional ethyl bromoacetate (0.20 mL, 0.29 g, 1.72 mmol) and Et3N (0.26 mL, 0.19 g, 1.89 mmol) were added and the reaction was stirred for an additional 6 days. The reaction was diluted with dichloromethane and washed with KHSO4 solution, NaHCO3 solution, and brine, dried over MgSO4, filtered and concentrated in vacuo yielding a clear oil. This oil was purified by flash chromatography yielding N-acetyl-N-[[4-(5-methyl-3-phenylisoxazol-4-yl)phenyl]sulfonyl]glycine, ethyl ester (0.243 g, 32%) as a clear colorless oil of suitable purity for use in the next step: 1H NMR (CDCl3/300 MHz) 8.03 (d, 2H, J=8.7 Hz), 7.47-7.27 (m, 9H), 4.61 (s, 2H), 4.21 (q, 2H, J=7.1 Hz), 2.51 (s, 3H), 2.33 (s, 3H), 1.28 (t, 3H, J=7.1 Hz). FABLRMS m/z 443 (M+H). FABHRMS m/z 442.1201 (M+, C22H22N2O6S Calc'd 442.1199).

Workup

  1. washwashed with KHSO4 solution, NaHCO3 solution, and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customyielding a clear oil
  6. customThis oil was purified by flash chromatography

Sources & evidence

ORD record
ord-2dfede1723324ea393c535542945f9a0
Source dataset
uspto-grants-2002_08
Patent number
US06436967B1

Reaction notes

Loading…