Triethylamine → Ethyl 5-(((tert-butoxycarbonyl)amino)methyl)-1,3,4-oxadiazole-2-carboxylate

HRID 966422노트

반응식

HRID 966422 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][NH:13][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[O:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][N:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 10108216Ethyl (N-{2-[(tert-butoxy)carbonylamino]acetylamino}carbamoyl)formate

생성물 1

HCID 10084542Ethyl 5-(((tert-butoxycarbonyl)amino)methyl)-1,3,4-oxadiazole-2-carboxylate수율 44.2%

시약·촉매·용매 2

HCID 5943Carbon Tetrachloride용매HCID 6344Dichloromethane용매

실험 절차

A solution of compound 7 (59 g, 200 mmol) and triethylamine (42 ml, 0.57 mol) in carbon tetrachloride (60 ml) is added to a stirred, room temperature of triphenylphosphine (63 g, 0.24 mol) in methylene chloride (900 ml). The reaction mixture is stirred for 30 minutes and then refluxed for 12 hours. After cooling to room temperature, the volatiles are removed in vacuo and the resulting residue is filtered through silica using methylene chloride:ethyl acetate (9:1) as the eluent. After removing the volatiles in vacuo, the crude product is purified by flash column chromatography over silica gel using methylene chloride:ethyl acetate (19:1) as the eluent. 24 g (44%) Of compound 8 is obtained as orange oil, which solidifies to a yellow solid on standing.

후처리

  1. temperaturerefluxed for 12 hours
  2. customthe volatiles are removed in vacuo
  3. filtrationthe resulting residue is filtered through silica
  4. customAfter removing the volatiles in vacuo
  5. customthe crude product is purified by flash column chromatography over silica gel

출처 및 근거

ORD 기록
ord-45471497c03e4d5e9a4605d130436714
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951946B2

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