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

HRID 1654327
Notes
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Reaction equation

HRID 1654327 reaction equation
ClC(Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[Cl-:13].ClCC[N:17]([C:21]1[CH:27]=[CH:26][C:24]([NH3+])=[CH:23][CH:22]=1)[CH2:18]CCl.[CH2:28]([N:30]([CH2:33]C)CC)[CH3:29].[NH2:35][C@H:36]([C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])[CH2:37][CH2:38][C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40].[CH:59]([Cl:62])(Cl)Cl>>[Cl:13][CH2:29][CH2:28][N:30]([CH:38]([C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])[CH2:37][C@@H:36]([C:49]([O:51][CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)=[O:50])[NH:35][C:18](=[O:4])[NH:17][C:21]1[CH:22]=[CH:23][CH:24]=[CH:26][CH:27]=1)[CH2:33][CH2:59][Cl:62]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 6212Chloroform2×HCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 3037947L-Glutamic acid dibenzyl esterHCID 702220824-[N,N-bis-(2-chloroethyl)amino]anilinium chloride

Product 1

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

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 rosylate 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°-122° 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-de4892b92b354183893d5d5453f19cfc
Source dataset
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05405990

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes