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

HRID 2258409
Notes
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Reaction equation

HRID 2258409 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2b03205782fd449f979d09c1771a542f
Source dataset
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05660829

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes