Sodium Hydroxide → (R)-3-(biphenyl-4-ylmethyl)-4-(2-carboxyethylamino)-4-oxobutanoic acid

HRID 1945024ノート

反応式

HRID 1945024 の反応式
[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([C:13]([NH:15][CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[O:14])[CH2:9][C:10]([OH:12])=[O:11])=[CH:3][CH:2]=1.[OH-].[Na+]>C1COCC1.CO>[C:1]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@@H:8]([C:13]([NH:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:14])[CH2:9][C:10]([OH:12])=[O:11])=[CH:5][CH:6]=1

参加物

5

反応物 2

HCID 14798Sodium Hydroxide2 回HCID 59607696(R)-3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoic acid

生成物 1

HCID 59607892(R)-3-(biphenyl-4-ylmethyl)-4-(2-carboxyethylamino)-4-oxobutanoic acid収率 76.9%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (R)-3-(biphenyl-4-ylmethyl)-4-(3-methoxy-3-oxopropylamino)-4-oxobutanoic acid (22.1 mg, 0.060 mmol) in THF (0.6 mL) and methanol (0.1 mL), aqueous 1M NaOH (0.12 mL, 0.12 mmol) is added at room temperature. After stirring for 3 hours, additional aqueous 1M NaOH (0.12 mL, 0.12 mmol) is added. The reaction mixture is allowed to stir for 30 minutes and quenched with 0.5 mL of aqueous 1M HCl and 0.5 mL of brine. The mixture is extracted twice with ethyl acetate, and the organic layer is concentrated under reduced pressure to give (R)-3-(biphenyl-4-ylmethyl)-4-(2-carboxyethylamino)-4-oxobutanoic acid (16.4 mg). HPLC retention time=1.04 minutes (condition A); MS (m+1)=356.1; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.13-2.31 (m, 3H) 2.59-2.65 (m, 1H) 2.81-2.90 (m, 2H) 3.12-3.27 (m, 2H) 7.26 (d, 2H, J=8 Hz) 7.34 (t, 1H, J=7.4 Hz) 7.45 (t, 2H, J=7.7 Hz) 7.57 (d, 2H, J=8.1 Hz) 7.63-7.65.

後処理

  1. stirringto stir for 30 minutes
  2. customquenched with 0.5 mL of aqueous 1M HCl and 0.5 mL of brine
  3. extractionThe mixture is extracted twice with ethyl acetate
  4. concentrationthe organic layer is concentrated under reduced pressure

出典と根拠

ORDレコード
ord-012158b361a642099da627dfc1af4dc9
出典データセット
uspto-grants-2013_03
特許番号
US08394853B2

反応ノート

読み込み中…