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Citric Acid → HCID 178523110、化合物

HRID 869654
ノート
印刷プレビュー

反応式

HRID 869654 の反応式
[F:1][C:2]([F:28])([F:27])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C@@H:12]2[CH2:16][O:17][C:18]2[C:19]([C:24]([NH2:26])=[O:25])=[N:20][CH:21]=[CH:22][CH:23]=2)=[O:10])[CH2:5][CH2:4]1.[H-].[Na+].I[CH2:32][C:33]1([OH:39])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN1CCCC1=O>[OH:39][C:33]1([CH2:32][NH:26][C:24](=[O:25])[C:19]2[C:18]([O:17][CH2:16][C@H:12]3[CH2:13][CH2:14][CH2:15][N:11]3[C:9]([C@H:6]3[CH2:7][CH2:8][C@H:3]([C:2]([F:1])([F:27])[F:28])[CH2:4][CH2:5]3)=[O:10])=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 669618924-(iodomethyl)tetrahydro-2H-pyran-4-olHCID 178513798HCID 178513798、化合物

生成物 1

HCID 178523110HCID 178523110、化合物収率 53.3%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone
溶媒

実験手順

To a solution of 3-(((R)-1-(trans-4-(trifluoromethyl)cyclohexanecarbonyl)pyrrolidin-2-yl)methoxy)picolinamide (105 mg, 0.263 mmol, EXAMPLE 75 Step 1) in 1-Methyl-2-pyrrolidone (5 mL) was added sodium hydride (60% oil dispersant, 16 mg, 0.394 mmol) at ambient temperature. After being stirred at room temperature for 1 h, 4-(iodomethyl)tetrahydro-2H-pyran-4-ol (76 mg, 0.315 mmol, EXAMPLE 77 Step 1) was added to the mixture. The mixture was heated at 70° C. and stirred for 3 days. After cooling to room temperature, aq. citric acid was added to the mixture. The mixture was extracted with ethyl acetate twice and washed successively with aq. sodium thiosulfate, aq. sodium bicarbonate, and brine. The extracts were combined and dried over sodium sulfate and concentrated in vacuo to afford 72 mg of crude oil. The residual oil was purified by preparative HPLC purification.

後処理

  1. temperatureThe mixture was heated at 70° C.
  2. stirringstirred for 3 days
  3. temperatureAfter cooling to room temperature
  4. extractionThe mixture was extracted with ethyl acetate twice
  5. washwashed successively with aq. sodium thiosulfate, aq. sodium bicarbonate, and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-bb22f43862cd429d814501d972bd77a9
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08969383B2

反応ノート

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