Ethyl Acetate → HCID 54108767、化合物

HRID 325598ノート

反応式

HRID 325598 の反応式
Cl.[NH2:2][C@H:3]([C:5]([N:7]1[CH2:14][CH2:13][CH2:12][C@H:8]1[C:9]([OH:11])=[O:10])=[O:6])[CH3:4].[C:15]([CH:23]=[CH:24][C:25]([OH:27])=[O:26])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+].CCOC(C)=O>CO.O.CC(O)=O.C(O)CCC>[C:25]([CH:24]([NH:2][C@H:3]([C:5]([N:7]1[CH2:14][CH2:13][CH2:12][C@H:8]1[C:9]([OH:11])=[O:10])=[O:6])[CH3:4])[CH2:23][C:15](=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([OH:27])=[O:26]

参加物

9

反応物 4

HCID 8857Ethyl AcetateHCID 94714Beta-benzoylacrylic acidHCID 516892Sodium BicarbonateHCID 12718469HCID 12718469、化合物

生成物 1

HCID 54108767HCID 54108767、化合物

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 2631-Butanol溶媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of L-alanyl-L-proline hydrochloride (2.26 g; 10.2 mmol) and 3-benzoylacrylic acid (1.97 g; 11.2 mmol) in methanol (50 ml) there was added sodium bicarbonate (1.71 g; 20.3 mmol) and the mixture was stirred for 48 hours. After filtration and evaporation, the residue was purified on DOWEX 50W-XY using 10:1 H2O:CH3OH and then 50:1 H2 :pyr as eluants. Freeze drying of the H2 :pyr fractions gave the product as a mixture (1:1) of diastereomers (2.68 g; 7.40 mmol; 73%). MS: m/e 461 (bis trimethylsilyl M⊕ -CO2TMS). TLC (silica gel; 3:1:1:1 EtOAc, BuOH, HOAc, H2O) Rf=0.35. NMR (D2O): 1.08 (minor), 1.18 (minor), 1.26, 1.34 (3H, 4×d, J=7) (2 rotomers); 1.5-2.2 (4H, m); 2.1-3.8 (4H, m); 3.9-4.3 (3H, m); 7.307.8 (5H,m).

後処理

  1. filtrationAfter filtration and evaporation
  2. customthe residue was purified on DOWEX 50W-XY using 10:1 H2O
  3. customFreeze drying of the H2
  4. custompyr fractions gave the product as a mixture (1:1) of diastereomers (2.68 g; 7.40 mmol; 73%)

出典と根拠

ORDレコード
ord-2387a110a3f74ecda75fc4f106f61c76
出典データセット
uspto-grants-1984_04
特許番号
US04442030

反応ノート

読み込み中…