Carbon Dioxide → HCID 178471411, 화합물

HRID 25592

반응식

HRID 25592 반응식
C(Cl)(=O)C(Cl)=O.C(=O)=O.CS(C)=O.[C:14]([O:18][C:19](=[O:32])[N:20]([C@H:22]1[CH2:27][CH2:26][C@H:25]([CH2:28][CH2:29][CH2:30]O)[CH2:24][CH2:23]1)[CH3:21])([CH3:17])([CH3:16])[CH3:15].CCN(CC)CC.C(OC(=O)N(C)[C@H]1CC[C@H](CCC=O)CC1)(C)(C)C.[CH3:59][CH2:60][O:61][C:62]([CH2:64]P(OCC)(OCC)=O)=[O:63].C[O-].[Na+]>C(Cl)Cl.CCOCC.C(O)C>[CH2:60]([O:61][C:62](=[O:63])[CH:64]=[CH:30][CH2:29][CH2:28][C@H:25]1[CH2:26][CH2:27][C@H:22]([N:20]([C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:32])[CH3:21])[CH2:23][CH2:24]1)[CH3:59]

참가 물질

12

반응물 8

HCID 280Carbon DioxideHCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 13345Triethyl phosphonoacetateHCID 65578Oxalyl chlorideHCID 10942334Sodium MethoxideHCID 178486041HCID 178486041, 화합물HCID 178486042HCID 178486042, 화합물

생성물 1

HCID 178471411HCID 178471411, 화합물수율 58%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

반응 조건

온도
-78 °C

실험 절차

1.4 ml (16.24 mmol) oxalylchloride was added to a dry-ice cooled solution (−78° C.) of 1.78 ml (25 mmol) DMSO in 40 ml CH2Cl2. After 10 min. stirring at −78° C., 2.39 g (12.49 mmol) of trans-[4-(3-Hydroxy-propyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester, dissolved in 5 ml CH2Cl2, was added. 15 min later, 8.7 ml (62.4 mmol) Et3N was added and the reaction-mixture was allowed to attain RT. The mixture was diluted with Et2O and then washed with 1N HCl and water. After evaporation of the solvents, a solution of crude trans-Methyl-[4-(3-oxo-propyl)-cyclohexyl]-carbamic acid tert-butyl ester (3.24 g, 12.02 mmol) and of 2.73 ml (13.3 mmol) triethyl phosphono acetate in 30 ml ethanol, was treated under ice-cooling with 1.37 g (24.05 mmol) NaOMe. The solution was stirred for 20 h at RT, and then concentrated in vacuo. The crude residue was dissolved in Et2O and washed with water. The organic layers were concentrated in vacuo and the crude product purified by chromatography on silica gel with EtOAc/Hexane 1:4 to yield 2.46 g (58%, 2 steps) of clean trans-5-[4-(tert-Butoxycarbonyl-methyl-amino)-cyclohexyl]-pent-2-enoic acid ethyl ester, MS: 339 (M).

후처리

  1. additionwas added
  2. customto attain RT
  3. washwashed with 1N HCl and water
  4. customAfter evaporation of the solvents
  5. stirringThe solution was stirred for 20 h at RT
  6. concentrationconcentrated in vacuo
  7. dissolutionThe crude residue was dissolved in Et2O
  8. washwashed with water
  9. concentrationThe organic layers were concentrated in vacuo
  10. customthe crude product purified by chromatography on silica gel with EtOAc/Hexane 1:4

출처 및 근거

ORD 기록
ord-5f96f3eaf2ac40319f944851794fe16c
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858651B2

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