Potassium Carbonate → 2-[N'-Benzyloxycarbonyl-N-(3,5-dimethyl-benzoyl)-hydrazino]-2-methyl-propionic acid ethyl ester

HRID 39655

반응식

HRID 39655 반응식
[CH2:1]([O:3][C:4](=[O:20])[C:5]([NH:8][NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])([CH3:7])[CH3:6])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH3:27][C:28]1[CH:29]=[C:30]([CH:34]=[C:35]([CH3:37])[CH:36]=1)[C:31](Cl)=[O:32]>C(Cl)Cl.O>[CH2:1]([O:3][C:4](=[O:20])[C:5]([N:8]([C:31](=[O:32])[C:30]1[CH:34]=[C:35]([CH3:37])[CH:36]=[C:28]([CH3:27])[CH:29]=1)[NH:9][C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])([CH3:7])[CH3:6])[CH3:2]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 810883,5-Dimethylbenzoyl ChlorideHCID 152825792-(N'-benzyloxycarbonyl-hydrazino)-2-methyl-propionic acid ethyl ester

생성물 1

HCID 598386122-[N'-Benzyloxycarbonyl-N-(3,5-dimethyl-benzoyl)-hydrazino]-2-methyl-propionic acid ethyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

반응 조건

온도
2.5 °C

실험 절차

2-(N′-benzyloxycarbonyl-hydrazino)-2-methyl-propionic acid ethyl ester (28 g, 0.1 mol) was dissolved in 50 mL CH2Cl2 and cooled on ice. A solution of 20.7 g K2CO3 in 30 mL of water was added. A solution of 3,5-dimethylbenzoyl chloride (17 g, 0.1 mol) in 50 mL of CH2Cl2 was added drop-wise over a period of 1 hour, maintaining the temperature at 0-5° C. The mixture was stirred for 1 hour on an ice bath, and then at room temperature overnight. TLC indicated the reaction was complete. The aqueous layer was removed in a separatory funnel and the organic phase was washed with water and then brine, and then dried over Na2SO4. The solvent was removed on a rotary evaporator. The residue was slurried in hexane, filtered, and then air-dried. 2-[N′-Benzyloxycarbonyl-N-(3,5-dimethyl-benzoyl)-hydrazino]-2-methyl-propionic acid ethyl ester was obtained as a white solid (35 g), giving a single spot by TLC. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.4 (s, 1H), 7.3 (m, 3H), 7.15 (m, 2H), 7.1 (s, 2H), 7.0 (s, 1H), 5.2 (d, 1H), 5.0 (d, 1H), 4.2 (m, 2H), 2.25 (s, 6H), 1.78 (s, 3H), 1.64 (s, 3H), 1.28 (t, 3H).

후처리

  1. temperaturecooled on ice
  2. customat room temperature
  3. customovernight
  4. customThe aqueous layer was removed in a separatory funnel
  5. washthe organic phase was washed with water
  6. dry with materialbrine, and then dried over Na2SO4
  7. customThe solvent was removed on a rotary evaporator
  8. filtrationfiltered
  9. customair-dried

출처 및 근거

ORD 기록
ord-a1712b34689c4c949e6e1fff9eb75a64
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524948B2

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