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Glycolic Acid → N-((2S)-3-{4-[3-(2-Cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-2-ethyl-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide

HRID 245121
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HRID 245121 반응식
[NH2:1][CH2:2][C@H:3]([OH:33])[CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[C:22]([O:24][CH3:25])[N:21]=[C:20]([CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[CH:19]=3)[N:14]=2)=[CH:8][C:7]=1[CH2:31][CH3:32].[C:34](O)(=[O:37])[CH2:35][OH:36].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CC(=O)OCC>[CH:26]1([C:20]2[CH:19]=[C:18]([C:15]3[N:14]=[C:13]([C:9]4[CH:10]=[C:11]([CH3:12])[C:6]([O:5][CH2:4][C@@H:3]([OH:33])[CH2:2][NH:1][C:35](=[O:36])[CH2:34][OH:37])=[C:7]([CH2:31][CH3:32])[CH:8]=4)[O:17][N:16]=3)[CH:23]=[C:22]([O:24][CH3:25])[N:21]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

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HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67491454(2S)-1-amino-3-{4-[3-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-2-ethyl-6-methyl-phenoxy}-propan-2-ol

생성물 1

HCID 49872362
N-((2S)-3-{4-[3-(2-Cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-2-ethyl-6-methyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide
수율 57.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (2S)-1-amino-3-{4-[3-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-2-ethyl-6-methyl-phenoxy}-propan-2-ol (100 mg, 220 μmol), glycolic acid (22 mg, 289 μmol) and DIPEA (86 mg, 666 μmol) in DMF (3 mL), TBTU (93 mg, 289 μmol) is added. The mixture is stirred at rt for 1 h before it is diluted with EA (50 mL) and washed with sat. aq. NaHCO3 solution (20 mL) followed by brine (20 mL). The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified by prep. HPLC to give the title compound (65 mg) as an almost colourless oil; LC-MS**: tR=0.84 min, [M+H]+=511.03; 1H NMR (CDCL3): δ1.33 (t, J=7.5 Hz, 3H), 1.68-1.79 (m, 2H), 1.82-1.95 (m, 4H), 2.05-2.15 (m, 2H), 2.41 (s, 3H), 2.76 (q, J=7.5 Hz, 2H), 3.18-3.28 (m, 1H), 3.49-3.59 (m, 1H), 3.75-3.95 (m, 3H), 4.01 (s, 3H), 4.18-4.26 (m, 3H), 7.08 (t, J=4.3 Hz, 1H), 7.49 (s, 1H), 7.91 (s, 1H), 7.93 (s, 1H).

후처리

  1. washwashed with sat. aq. NaHCO3 solution (20 mL)
  2. extractionextract
  3. dry with materialis dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by prep

출처 및 근거

ORD 기록
ord-82604757e58c458d9166c918dc7efd4d
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08658675B2

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