Ethyl oxoacetate → (3R-trans)-[(6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4yl)amino]acetic acid, ethyl ester

HRID 356672ノート

反応式

HRID 356672 の反応式
[NH2:1][C@H:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[C@@H:3]1[OH:16].[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=O.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.C(O)(=O)C>[C:12]([C:9]1[CH:10]=[CH:11][C:6]2[O:5][C:4]([CH3:14])([CH3:15])[C@H:3]([OH:16])[C@@H:2]([NH:1][CH2:18][C:17]([O:21][CH2:22][CH3:23])=[O:20])[C:7]=2[CH:8]=1)#[N:13]

参加物

7

反応物 4

HCID 70211Ethyl oxoacetateHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 14511095(3R,4S)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile

生成物 1

HCID 10756893(3R-trans)-[(6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4yl)amino]acetic acid, ethyl ester

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

To a solution of (3R-trans)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile (the title A compound) and ethyl glyoxylate (2.5 g) in methanol (30 mL) and acetic acid (2 mL) at 0° C. under argon atmosphere was added sodium cyanoborohydride (1.5 g). The reaction mixture was stirred at 0 C. for 30 minutes, poured into saturated sodium bicarbonate (150 mL) and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated. The residue was purified by chromatography to give an oil, which solidified upon standing (1.8 g, 48%).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography
  5. customto give an oil, which

出典と根拠

ORDレコード
ord-2c67c7dc40684817bfea479c176dc261
出典データセット
uspto-grants-1998_11
特許番号
US05837702

反応ノート

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