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Toluene → Ethyl 3-(((benzyloxy)carbonyl)amino)-2,5-dioxopyrrolidine-3-carboxylate

HRID 1158260
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HRID 1158260 반응식
[I-].[Na+].Cl[CH2:4][C:5]([NH2:7])=[O:6].C1(C)C=CC=CC=1.[CH2:15]([O:22][C:23]([NH:25][CH:26]([C:32]([O:34]CC)=O)[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O-]CC.[Na+]>C(O)C>[CH2:15]([O:22][C:23]([NH:25][C:26]1([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:4][C:5](=[O:6])[NH:7][C:32]1=[O:34])=[O:24])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1
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참가 물질

7

반응물 5

HCID 1140TolueneHCID 5238Sodium IodideHCID 6580ChloroacetamideHCID 259787Diethyl 2-(benzyloxycarbonylamino)malonateHCID 2723922Sodium ethoxide

생성물 1

HCID 10267979Ethyl 3-(((benzyloxy)carbonyl)amino)-2,5-dioxopyrrolidine-3-carboxylate수율 72%

시약·촉매·용매

1
HCID 702Ethanol용매2회

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온도
0 °C

실험 절차

To 123 kg of ethanol, 25.0 kg (167 mol) of sodium iodide and 14.2 kg (152 mol) of α-chloroacetamide were added and the resultant mixture was heated to 77° C. and was stirred for 3 hours. To the resultant suspension, 58.2 kg (130 mol) of 69% toluene solution of diethyl 2-benzyloxycarbonylaminomalonate was added, followed by cooling the resultant mixture to 0° C. Thereto, 89.1 kg (262 mol) of 20% ethanol solution of sodium ethoxide was dropped for 3 hours while maintaining the temperature at 0° C. After the reaction mixture was stirred for 3 hours at 0° C., the reaction was quenched by adding 7.9 kg of acetic acid and 15.1 kg of 85% phosphoric acid to the reaction mixture and the solvent was distilled off under reduced pressure. To the reaction mixture, 200 kg of toluene and 80 kg of water were added and the phase separation of the reaction mixture was performed. After the organic phase was washed with water 3 times, it was quantitatively analyzed and the yield of 2-benzyloxycarbonylamino-2-ethoxycarbonyl succinimide was found to be 87.5%. This solution was concentrated and then was recrystallized with toluene and ethanol to thereby obtaining 30 kg (yield: 72%) of 2-benzyloxycarbonylamino-2-ethoxycarbonyl succinimide as a white crystal.

후처리

  1. stirringAfter the reaction mixture was stirred for 3 hours at 0° C.
  2. customthe reaction was quenched
  3. additionby adding 7.9 kg of acetic acid and 15.1 kg of 85% phosphoric acid to the reaction mixture
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the reaction mixture, 200 kg of toluene and 80 kg of water were added
  6. customthe phase separation of the reaction mixture
  7. washAfter the organic phase was washed with water 3 times, it
  8. concentrationThis solution was concentrated
  9. customwas recrystallized with toluene and ethanol

출처 및 근거

ORD 기록
ord-b10f1611c4d048c0b5848c2196182558
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07807846B2

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