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Sodium Hydroxide → 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxy piperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylic acid

HRID 655740
ノート
印刷プレビュー

反応式

HRID 655740 の反応式
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:35]([O:37]CC)=[O:36])=[C:21]([C:23]3[CH:28]=[N:27][C:26]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:25][N:24]=3)[N:22]=2)[CH2:14][C@@H:13]1[O:40][CH2:41][CH3:42])=[O:10].[OH-].[Na+]>CO>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]([C:35]([OH:37])=[O:36])=[C:21]([C:23]3[CH:28]=[N:27][C:26]([N:29]4[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]4)=[CH:25][N:24]=3)[N:22]=2)[CH2:14][C@@H:13]1[O:40][CH2:41][CH3:42])=[O:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 59402461ethyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylate

生成物 1

HCID 594025252-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxy piperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylic acid収率 31.8%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

To the solution of ethyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylate (Example 67, 120 mg, 0.188 mmol) in methanol (20 mL) was added 2N sodium hydroxide (3 mL) in a dropwise fashion at 0° C. The reaction mixture was stirred overnight and then concentrated under reduced pressure to dryness. The resulting residue was diluted with water (20 mL) and extracted with ethyl acetate to remove any organic impurities. The aqueous layer was passed through celite bed and acidified with 2N hydrochloric acid. The precipitated product was collected by filtration and dried to afford 35 mg (31.8%) of 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-ethoxy piperidin-1-yl]-4-[5-(piperidin-1-yl)pyrazin-2-yl]-1,3-thiazole-5-carboxylic acid as a yellow solid.

後処理

  1. concentrationconcentrated under reduced pressure to dryness
  2. additionThe resulting residue was diluted with water (20 mL)
  3. extractionextracted with ethyl acetate
  4. customto remove any organic impurities
  5. filtrationThe precipitated product was collected by filtration
  6. customdried

出典と根拠

ORDレコード
ord-fae2bf4e7a584e38937584258980d524
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08071605B2

反応ノート

読み込み中…

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