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Triethylamine → dibenzyl 4-[N,N-bis(2-chloroethyl)amino]phenylcarbamoyl-L-glutamate

HRID 1081550
ノート
印刷プレビュー

反応式

HRID 1081550 の反応式
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[Cl-].[Cl:14][CH2:15][CH2:16][N:17](C1C=CC([NH3+])=CC=1)[CH2:18][CH2:19][Cl:20].C([N:30](CC)CC)C.S([C:39]1[CH:45]=[CH:44][C:42](C)=[CH:41][CH:40]=1)(O)(=O)=O.[NH2:46][C@H:47]([C:60]([O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)=[O:61])[CH2:48][CH2:49][C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51]>C(Cl)(Cl)Cl>[Cl:20][CH2:19][CH2:18][N:17]([CH:49]([C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:48][C@@H:47]([C:60]([O:62][CH2:63][C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1)=[O:61])[NH:46][C:5](=[O:11])[NH:30][C:39]1[CH:40]=[CH:41][CH:42]=[CH:44][CH:45]=1)[CH2:16][CH2:15][Cl:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8471Triethylamine2 回HCID 94429TriphosgeneHCID 13233366L-Glutamic acid dibenzyl ester tosylateHCID 702220824-[N,N-bis-(2-chloroethyl)amino]anilinium chloride

生成物 1

HCID 70224102dibenzyl 4-[N,N-bis(2-chloroethyl)amino]phenylcarbamoyl-L-glutamate

試薬・触媒・溶媒 1

HCID 6212
Chloroform
溶媒
2 回

実験手順

To a solution of triphosgene (1 g) in chloroform (80 ml) was added at 10° C. 4-[N,N-bis-(2-chloroethyl)amino]anilinium chloride (2.7 g). Whilst keeping the temperature at 10° C., triethylamine (4.15 ml) was added and the mixture was stirred and allowed to warm to ambient temperature for 15 minutes. To this mixture was added in one portion dibenzyl glutamate tosylate and triethylamine (1.7 ml). After 1.5 hours at ambient temperature the mixture was diluted with chloroform (100 ml), washed twice with water, dried and evaporated to dryness. The residue was chromatographed on Merck silica gell Art 9385, eluting with ethyl acetate hexane to give dibenzyl 4[N,N-bis(2-chloroethyl)amino]-phenylcarbamoyl-L-glutamate (2.5 g). m.p. 119°-22° C.

後処理

  1. customat 10° C.
  2. washwashed twice with water
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was chromatographed on Merck silica gell Art 9385
  6. washeluting with ethyl acetate hexane

出典と根拠

ORDレコード
ord-222277783f35493ab30ace28da3f5b66
出典データセット
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05587161

反応ノート

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