Dicyclohexylcarbodiimide → HCID 21437119, compound

HRID 2397204Notes

Reaction equation

HRID 2397204 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:31][N:32]1[C:38]2[CH:39]=[CH:40][C:41]([Cl:43])=[CH:42][C:37]=2[CH:36]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:35]([NH2:50])[CH2:34][C:33]1=[O:51]>C(OCC)(=O)C>[CH3:31][N:32]1[C:38]2[CH:39]=[CH:40][C:41]([Cl:43])=[CH:42][C:37]=2[CH:36]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:35]([NH:50][C:13](=[O:15])[CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:34][C:33]1=[O:51]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 21437113HCID 21437113, compound

Product 1

HCID 21437119HCID 21437119, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4.2 g. (0.02 moles) of benzyloxycarbonyl-glycine and 4.0 g. (0.02 moles) of dicyclohexyl carbodiimide are added to a solution of 6.0 g. (0.02 moles) of 1-methyl-4-amino-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one in 200 ml. of ethyl acetate. The reaction mixture is stirred at room temperature overnight, thereafter the separated dicyclohexyl urea is filtered off, and the filtrate is evaporated under reduced pressure. The residue is admixed with acetonitrile, the solution is boiled, the separated dicyclohexyl urea is filtered off from the hot solution, and the filtrate is allowed to cool. The separated crude product is filtered off, and crystallized from ethanol. 7.1 g. (72%) of 1-methyl-4-(N-benzyloxycarbonyl-glycylamino)-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one are obtained; m.p.: 184°-190° C.; Rf(1) = 0.3.

Workup

  1. filtrationthe separated dicyclohexyl urea is filtered off
  2. customthe filtrate is evaporated under reduced pressure
  3. filtrationthe separated dicyclohexyl urea is filtered off from the hot solution
  4. temperatureto cool
  5. customThe separated crude product
  6. filtrationis filtered off
  7. customcrystallized from ethanol

Sources & evidence

ORD record
ord-8e286fe37f3046cfb34a4f853959d5be
Source dataset
uspto-grants-1977_05
Patent number
US04021421

Reaction notes

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