Ethyl bromoacetate → HCID 59656591, 화합물

HRID 2054757노트

반응식

HRID 2054757 반응식
[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]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 24901496HCID 24901496, 화합물

생성물 1

HCID 59656591HCID 59656591, 화합물

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A solution of (1S)-1-{[(2S)-4-(2,5-difluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrol-1-yl]carbonyl}-2,2-dimethylpropylamine (6-1, 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 min. 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 (7-1) as an off-white solid. LRMS m/z (M+H) 457.5 found, 457.2 required.

후처리

  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

출처 및 근거

ORD 기록
ord-5884c74d3d9a4ee4acd19679cc880582
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07329762B2

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