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

HRID 966422ノート

反応式

HRID 966422 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-45471497c03e4d5e9a4605d130436714
出典データセット
uspto-grants-2005_10
特許番号
US06951946B2

反応ノート

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