HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1081550
Notes
Print preview

Reaction equation

HRID 1081550 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 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.

Workup

  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

Sources & evidence

ORD record
ord-222277783f35493ab30ace28da3f5b66
Source dataset
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05587161

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes