Hydrochloric Acid → HCID 57920038, 화합물

HRID 19199노트

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HRID 19199 반응식
[Cl:1][C:2]1[CH:39]=[CH:38][CH:37]=[CH:36][C:3]=1[O:4][C:5]1[CH2:9][N:8]([C@@H:10]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[C:11]([NH:13][C:14]2[CH:18]=[CH:17][N:16]([CH2:19][C@@H:20]3[CH2:24][O:23]C(C)(C)[O:21]3)[N:15]=2)=[O:12])[C:7](=[O:35])[CH:6]=1.Cl.ClC1C=CC=CC=1OC1CN([C@@H](CC2C=CC(Cl)=CC=2)C(NC2C=CN(C[C@@H](O)CO)N=2)=O)C(=O)C=1>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:39]=[CH:38][CH:37]=[CH:36][C:3]=1[O:4][C:5]1[CH2:9][N:8]([C@@H:10]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[C:11]([NH:13][C:14]2[CH:18]=[CH:17][N:16]([CH2:19][C@@H:20]([OH:21])[CH2:24][OH:23])[N:15]=2)=[O:12])[C:7](=[O:35])[CH:6]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 57920149(S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-N-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-3-(2-chlorophenyl)-propionamideHCID 66899237HCID 66899237, 화합물

생성물 1

HCID 57920038HCID 57920038, 화합물

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
25 °C

실험 절차

A solution of (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(4-chlorophenyl)-propionic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-amide (prepared as in Example 188, 0.151 g, 0.259 mmol) in tetrahydrofuran (3 mL) was treated with 2N aqueous hydrochloric acid solution (3 mL). The reaction mixture was stirred at 25° C. for 3 h. The reaction mixture was diluted with ethyl acetate, washed with water, saturated sodium bicarbonate solution, a saturated sodium chloride solution and dried over magnesium sulfate. The organic layer was concentrated to afford, (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-(4-chlorophenyl)-N-[1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-propionamide (0.110 g, 80%) as a white powder: HR-ES-MS m/z calculated for C25H24Cl2N4O5 [M+H]+ 531.1196, observed 531.1197; 1H NMR (300 MHz, DMSO-d6); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.19-3.30 (m, 4H), 3.74 (br. s., 1H), 3.80-3.91 (m, 1H), 4.07 (dd, J=13.6, 3.6 Hz, 1H), 4.25 (d, J=18.2 Hz, 1H), 4.39 (d, J=18.2 Hz, 1H), 4.65-4.71 (m, 1H), 4.72 (s, 1H), 4.93 (d, J=5.1 Hz, 1H), 5.18 (t, J=7.5 Hz, 1H), 6.43 (d, J=1.5 Hz, 1H), 7.18-7.30 (m, 2H), 7.30-7.47 (m, 5H), 7.53 (d, J=1.5 Hz, 1H), 7.62 (d, J=7.8 Hz, 1H), 10.76 (s, 1H).

후처리

  1. washwashed with water, saturated sodium bicarbonate solution
  2. dry with materiala saturated sodium chloride solution and dried over magnesium sulfate
  3. concentrationThe organic layer was concentrated
  4. customto afford

출처 및 근거

ORD 기록
ord-d01749b3a6cb4d3bace1ecbd614d346d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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