Ethyl bromoacetate → HCID 59656591, compound

HRID 1394948Notes

Reaction equation

HRID 1394948 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([C@@H:16]([NH2:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:10]=1.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C(N(CC)C(C)C)(C)C>CCCCO>[C:17]([C@H:16]([NH:21][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[C:14]([N:12]1[CH2:13][C:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])=[CH:10][C@H:11]1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 24901496HCID 24901496, compound

Product 1

HCID 59656591HCID 59656591, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (1S)-1-{[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]carbonyl}-2,2-dimethylpropylamine (16-1, 325 mg, 0.877 mmol, 1 equiv), ethyl bromoacetate (0.195 mL, 1.76 mmol, 2.00 equiv), and N,N-diisopropylethylamine (0.613 mL, 3.51 mmol, 4.00 equiv) in n-BuOH (4.0 mL) was heated under microwave irradiation at 150° C. for 15 minutes. The reaction mixture was concentrated and the residue was partitioned between a ethyl acetate (100 mL) and a 1:1 mixture of saturated aqueous potassium bisulfate solution and brine (100 mL). The organic layer was then washed with saturated aqueous sodium bicarbonate solution (100 mL) followed by brine (100 mL), then dried over magnesium sulfate and concentrated to give ethyl({(1S)-1-tert-butyl-2-[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]-2-oxoethyl}amino)acetate (30-1) as an off-white solid. LRMS m/z (M+H) 457.5 found, 457.2 required.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between a ethyl acetate (100 mL)
  3. additiona 1:1 mixture of saturated aqueous potassium bisulfate solution and brine (100 mL)
  4. washThe organic layer was then washed with saturated aqueous sodium bicarbonate solution (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-070c5081de964a15af5216f37c03f787
Source dataset
uspto-grants-2008_03
Patent number
US07348440B2

Reaction notes

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