Water → (4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetic acid ethyl ester

HRID 76035

반응식

HRID 76035 반응식
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:23])[CH2:19][N:20]=[N+]=[N-])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:44][C:45]1[CH:50]=[CH:49][CH:48]=[C:47]([N:51]=[C:52]=S)[CH:46]=1.O>O1CCOCC1.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[O:23][C:52]([NH:51][C:47]4[CH:48]=[CH:49][CH:50]=[C:45]([Cl:44])[CH:46]=4)=[N:20][CH:19]=3)=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)[CH3:2]

참가 물질

7

반응물 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 754493-Chlorophenyl isothiocyanateHCID 86634688HCID 86634688, 화합물

생성물 1

HCID 66615762(4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetic acid ethyl ester수율 63.8%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

To a solution of {4-[4-(2-azidoacetyl)-phenyl]-cyclohexyl}-acetic acid ethyl ester (154 mg, 0967 mmol) in 1,4-dioxane (5 mL) is added triphenylphosphine (122 mg, 0.967 mmol) and 1-chloro-3-isothiocyanatobenzene (0.051 mL, 0.389 mmol). The reaction mixture is then heated at 90° C. for 30 min. Water (10 mL) is added and EtOAc (20 mL) is used to extract. The organic phase is washed with brine (1×15 mL), dried with MgSO4, and concentrated to give the title compound (109 mg) as an off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 1.19 (t, J=7.20 Hz, 3H) 1.12-1.19 (m, 2H) 1.43-1.52 (m, 2H) 1.81 (d, J=10.61 Hz, 4H) 1.73-1.84 (m, 1H) 2.23 (d, J=6.82 Hz, 2H) 4.07 (q, J=7.07 Hz, 2H) 6.99 (ddd, J=7.83, 2.02, 0.76 Hz, 1H) 7.28-7.36 (m, 3H) 7.41 (s, 1H) 7.47-7.53 (m, 3H) 7.85 (t, J=2.02 Hz, 1H) 10.52 (s, 1H); (M+H)+439.2.

후처리

  1. extractionto extract
  2. washThe organic phase is washed with brine (1×15 mL)
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-635c57ece56f443ab8df8330afc5c1b1
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835451B2

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