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

HRID 1898981Notes

Reaction equation

HRID 1898981 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][CH2:10][NH:11][C:12](=[O:30])[CH2:13][NH:14][CH2:15][C:16]2[CH:21]=[CH:20]C(OCC3C=CC=CC=3)=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:31]([NH:41][C@H:42]([C:49]([OH:51])=O)[CH2:43][C:44]1[N:48]=[CH:47][NH:46][CH:45]=1)([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32].C(N[C@@H](C(O)=O)CC1N=CNC=1)([O:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)=O>>[C:35]1([CH2:34][O:33][C:31]([NH:41][C@H:42]([C:49]([N:14]([CH2:15][CH2:16][CH2:21][CH2:20][O:54][CH2:55][C:56]2[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=2)[CH2:13][C:12]([NH:11][CH2:10][CH2:9][O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:30])=[O:51])[CH2:43][C:44]2[N:48]=[CH:47][NH:46][CH:45]=2)=[O:32])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 3

HCID 70182186N-[2-(Phenylmethoxy)ethyl]-N2-[[4-(phenylmethoxy)phenyl]methyl]glycinamideHCID 178523877HCID 178523877, compoundHCID 178523878Z-D-His-OH

Product 1

HCID 178521320N-[(Phenylmethoxy)carbonyl]-L-histidyl-N2-[4-(phenylmethoxy)butyl]-N-[2-(phenylmethoxy)ethyl]glycinamide

Procedure

According to Example 10, Step 4, by substituting the compound from Step 1 above for N-[2-(phenylmethoxy)ethyl]-N2 -[[4-(phenylmethoxy)phenyl]methyl]glycinamide and CBZ-histidine for CBZ-D-histidine, the title compound was obtained as a white foam; ES-MS 642 (m+1).

Sources & evidence

ORD record
ord-eb0ed910c1a84304ae83fb373342fba5
Source dataset
uspto-grants-1996_11
Patent number
US05571792

Reaction notes

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