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

HRID 655732ノート

反応式

HRID 655732 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:29]([O:31]C)=[O:30])=[C:21]([C:23]3[N:27]([CH3:28])[N:26]=[CH:25][N:24]=3)[N:22]=2)[CH2:14][C@@H:13]1[O:33][CH2:34][CH:35]=[CH2:36])=[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:29]([OH:31])=[O:30])=[C:21]([C:23]3[N:27]([CH3:28])[N:26]=[CH:25][N:24]=3)[N:22]=2)[CH2:14][C@@H:13]1[O:33][CH2:34][CH:35]=[CH2:36])=[O:10]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 46234299methyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate

生成物 1

HCID 462359882-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylic acid収率 72%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of methyl 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylate (Example 30, 90 mg, 0.162 mmol) and 2N sodium hydroxide (4 mL) in methanol (30 mL) was stirred at room temperature for 4 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in water, which was acidified to pH 3 with 2 N hydrochloric acid (2 mL). The resulting solid was collected by filtration and dried to afford 2-[(3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidin-1-yl]-4-(1-methyl-1H-1,2,4-triazol-5-yl)-1,3-thiazole-5-carboxylic acid (40 mg, 72%) as solid.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in water
  3. filtrationThe resulting solid was collected by filtration
  4. customdried

出典と根拠

ORDレコード
ord-0b81137b24854d528107d9d45d346b21
出典データセット
uspto-grants-2011_12
特許番号
US08071605B2

反応ノート

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