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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
ノート
印刷プレビュー

反応式

HRID 245121 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 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
収率 57.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-82604757e58c458d9166c918dc7efd4d
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658675B2

反応ノート

読み込み中…

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