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

HRID 651204
ノート
印刷プレビュー

反応式

HRID 651204 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 tempeature 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 tempeature the mixture was diluted with chloroform (100 ml), washed twice with water, dried and evaporated to dryness. The resdiue 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 resdiue 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-b1a519147fb3490f99d7dd4a5c982a30
出典データセット
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06277880B1

反応ノート

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