Dicyclohexylcarbodiimide → N-[(Phenylmethoxy)carbonyl]-D-histidyl-N-[2-(phenylmethoxy)ethyl]-N2-[[4-(phenylmethoxy)phenyl]methyl]glycinamide

HRID 1898979Notes

Reaction equation

HRID 1898979 reaction equation
[C:1]([NH:11][C@@H:12]([C:19]([OH:21])=O)[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1C=C2N=NN(O)C2=CC=1.O.C1CCC(N=C=NC2CCCCC2)CC1.[C:48]1([CH2:54][O:55][CH2:56][CH2:57][NH:58][C:59](=[O:77])[CH2:60][NH:61][CH2:62][C:63]2[CH:68]=[CH:67][C:66]([O:69][CH2:70][C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)=[CH:65][CH:64]=2)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C=O)C>[C:5]1([CH2:4][O:3][C:1]([NH:11][C@@H:12]([C:19]([N:61]([CH2:62][C:63]2[CH:64]=[CH:65][C:66]([O:69][CH2:70][C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)=[CH:67][CH:68]=2)[CH2:60][C:59]([NH:58][CH2:57][CH2:56][O:55][CH2:54][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:77])=[O:21])[CH2:13][C:14]2[N:18]=[CH:17][NH:16][CH:15]=2)=[O:2])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 70182186N-[2-(Phenylmethoxy)ethyl]-N2-[[4-(phenylmethoxy)phenyl]methyl]glycinamideHCID 178523878Z-D-His-OH

Product 1

HCID 178521308N-[(Phenylmethoxy)carbonyl]-D-histidyl-N-[2-(phenylmethoxy)ethyl]-N2-[[4-(phenylmethoxy)phenyl]methyl]glycinamideYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of CBZ-D-histidine (0.093 g, 0.32 mmol) in DMF (2 mL) was added HOBT hydrate (0.059 g, 0.39 mmol) followed by DCC (0.080 g, 0.39 mmol). A solution of the compound from Step 3 above (0.13 g, 0.32 mmol) in DMF (2 mL) was added and the mixture was stirred overnight at room temperature. The mixture was filtered, and the filtrate was diluted with CHCl3, washed twice with saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated. Flash chromatography (2-5% MeOH/CHCl3) gave 0.10 g (45%) of the title compound as a white powder; ES-MS 676 (m+1).

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with CHCl3
  3. washwashed twice with saturated aqueous NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a731391f76aa4670962998a005fc5a41
Source dataset
uspto-grants-1996_11
Patent number
US05571792

Reaction notes

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