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Lithium Hydroxide → HCID 10119718、化合物

HRID 2085665
ノート
印刷プレビュー

反応式

HRID 2085665 の反応式
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17]C)=O)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].[CH:23]1([NH:29][C:30]2[CH:35]=[CH:34][C:33]([S:36]([NH2:39])(=[O:38])=[O:37])=[CH:32][C:31]=2[N+:40]([O-:42])=[O:41])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.CCN=C=NCCCN(C)C>C1COCC1.CN(C1C=CN=CC=1)C.O1CCOCC1.C(OCC)(=O)C>[C:1]([CH:5]1[CH2:6][CH2:7][CH:8]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([NH:39][S:36]([C:33]3[CH:34]=[CH:35][C:30]([NH:29][CH:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[C:31]([N+:40]([O-:42])=[O:41])[CH:32]=3)(=[O:38])=[O:37])=[O:17])=[CH:13][CH:12]=2)[CH2:9][CH2:10]1)([CH3:3])([CH3:4])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 3939Lithium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22660807HCID 22660807、化合物HCID 22730084HCID 22730084、化合物

生成物 1

HCID 10119718HCID 10119718、化合物

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine
触媒
HCID 8028Tetrahydrofuran溶媒
HCID 8857Ethyl Acetate溶媒
HCID 312751,4-Dioxane溶媒

実験手順

A mixture of Example 5C (55 mg, 0.20 mmol) and 1M LiOH (0.3 mL) in THF (2 mL) was heated to 50° C., stirred for 3 hours, concentrated, dissolved in DMF (0.5 mL), and treated with a mixture of Example 3A (60 mg, 0.20 mmol), EDCI (96 mg, 0.50 mmol), and DMAP (10 mg) in dioxane (2.0 mL). The mixture was stirred for 16 hours, diluted with ethyl acetate (50 mL), washed sequentially with 1M HCl (5 mL), water (5 mL), and brine (5 mL), dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel, with 50% ethyl acetate/hexanes to provide a ˜2:1 mixture of diastereomers. MS (ESI(−)) m/e 540 (M−H)−; 1H NMR (400 MHz, DMSO-d6) δ8.63 (2d, 1H total), 8.33 (2d, 1H total), 7.95 (m, 1H), 7.82 and 7.78 (2d, 2H total), 7.45 (m, 1H), 7.30 (m, 2H), 3.71 (m, 1H), 2.28-0.95 (m, 20H), 0.86 and 0.75 (2s, 9H total).

後処理

  1. concentrationconcentrated
  2. dissolutiondissolved in DMF (0.5 mL)
  3. stirringThe mixture was stirred for 16 hours
  4. washwashed sequentially with 1M HCl (5 mL), water (5 mL), and brine (5 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel, with 50% ethyl acetate/hexanes
  9. customto provide
  10. additiona ˜2:1 mixture of diastereomers

出典と根拠

ORDレコード
ord-f62fefd0a6c04aab9c2b0550472d9577
出典データセット
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06720338B2

反応ノート

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