Lithium hydroxide, monohydrate → 7-[(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylic acid

HRID 132881ノート

反応式

HRID 132881 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[F:40])[CH2:10][C:11]([N:13]1[CH2:22][C:21]2[N:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]([C:27]([O:29]CC)=[O:28])=[CH:17][C:16]=2[CH2:15][CH2:14]1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>O1CCCC1.CO.O>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[F:40])[CH2:10][C:11]([N:13]1[CH2:22][C:21]2[N:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]([C:27]([OH:29])=[O:28])=[CH:17][C:16]=2[CH2:15][CH2:14]1)=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 69222346Ethyl 7-[(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylate

生成物 1

HCID 692244927-[(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoyl]-2-(trifluoromethyl)-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 21892291Methanol tetrahydrofuran water溶媒

実験手順

A solution of the product from Step A above (92 mg, 0.161 mmol) in 1.2 mL of 3:2:1 tetrahydrofuran/methanol/water was treated with lithium hydroxide monohydrate (10 mg) and the solution was stirred at room temperature for 18 h. The volatiles were removed under a stream of nitrogen, and the residue was dissolved in 4 mL of water. The solution was acidified by portionwise addition of citric acid monohydrate, and the product was extracted into ethyl acetate. The combined organic extracts were dried over magnesium sulfate and concentrated to afford the title compound as a white foam.

後処理

  1. customThe volatiles were removed under a stream of nitrogen
  2. dissolutionthe residue was dissolved in 4 mL of water
  3. additionThe solution was acidified by portionwise addition of citric acid monohydrate
  4. extractionthe product was extracted into ethyl acetate
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-3b98789a5fe54851a756c4cb22efb505
出典データセット
uspto-grants-2008_06
特許番号
US07388019B2

反応ノート

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