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

HRID 356672노트

반응식

HRID 356672 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-2c67c7dc40684817bfea479c176dc261
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05837702

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