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Triethylamine → HCID 178470087、化合物

HRID 1093075
ノート
印刷プレビュー

反応式

HRID 1093075 の反応式
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:20]2[NH:21][C:22](=O)[C:23]([OH:31])=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:25]=2)[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][S:34](Cl)(=[O:36])=[O:35].C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:20]2[NH:21][CH2:22][C:23]([O:31][S:34]([CH3:33])(=[O:36])=[O:35])=[C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[N:25]=2)[CH2:17][CH2:16][CH:15]([CH2:18][O:19][S:34]([CH3:33])(=[O:36])=[O:35])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 136061329HCID 136061329、化合物

生成物 1

HCID 178470087HCID 178470087、化合物収率 815.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a stirred solution of ethyl 2-(1-(benzyloxycarbonylamino)-4-(hydroxymethyl)cyclohexyl)-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxylate (1.85 g, 4.15 mmol) in THF (40 mL) cooled to 0° C. was added methanesulfonyl chloride (0.96 mmol, 12.45 mmol) and triethylamine (1.79 mL, 12.87 mmol). The mixture was allowed to warm to room temperature and stirred for 18 h. The resulting precipitate was filtered off and washed with THF. The filtrate and washings were concentrated to afford an amber oil. A solution of this oil in methanol (10 mL) was treated with K2CO3 (574 mg, 4.15 mmol) at room temperature for 3 h. The mixture was then concentrated and the residue was dissolved in ethyl acetate (200 mL), washed with 1N HCl (100 mL) followed by brine (100 mL), then dried (Na2SO4), filtered and concentrated to give 2.3 g of title compound as a yellow oil. LCMS (M+H)=602.45.

後処理

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with THF
  3. concentrationThe filtrate and washings were concentrated
  4. customto afford an amber oil
  5. concentrationThe mixture was then concentrated
  6. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  7. washwashed with 1N HCl (100 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-e81b67721eaf42ca9336a422de6a6a52
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08129398B2

反応ノート

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