Cyclohexaneacetic acid → N-[N-(Cyclohexylacetyl)-L-alaninyl]-L-phenylalanine Methyl Ester

HRID 983288Notes

Reaction equation

HRID 983288 reaction equation
[CH:1]1([CH2:7][C:8]([OH:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:11][O:12][C:13](=[O:28])[C@H:14]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH:15][C:16](=[O:20])[C@H:17]([CH3:19])[NH2:18].C(N[C@H](C(O)=O)C)(OC(C)(C)C)=O.Cl.COC(=O)[C@H](CC1C=CC=CC=1)N>>[CH3:11][O:12][C:13](=[O:28])[C@H:14]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH:15][C:16](=[O:20])[C@H:17]([CH3:19])[NH:18][C:8](=[O:10])[CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 4

HCID 21363Cyclohexaneacetic acidHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 85082Tert-butoxycarbonylalanineHCID 12988705Alanylphenylalanine methyl ester

Product 1

HCID 9799725N-[N-(Cyclohexylacetyl)-L-alaninyl]-L-phenylalanine Methyl Ester

Procedure

Following General Procedure U and using cyclohexylacetic acid (Aldrich) and N-(L-alaninyl)-L-phenylalanine methyl ester (prepared by coupling N-BOC-L-alanine (Bachem) with L-phenylalanine methyl ester hydrochloride (Bachem) using General Procedure U, followed by removal of the BOC-group using General Procedure Y), the title compound was prepared as a solid (mp=156-158° C.). The reaction was monitored by tlc (Rf=0.25 in 1:1 EtOAc/hexanes).

Workup

  1. customprepared
  2. customfollowed by removal of the BOC-group
  3. customwas prepared as a solid (mp=156-158° C.)

Sources & evidence

ORD record
ord-b7b472b718ef41c8bc028d3a2cf2d337
Source dataset
uspto-grants-2005_03
Patent number
US06861558B2

Reaction notes

Loading…