Cyclopentylacetic acid → N-[N-(Cyclopentylacetyl)-L-alaninyl]-L-phenylalanine Methyl Ester

HRID 2180798Notes

Reaction equation

HRID 2180798 reaction equation
[CH:1]1([CH2:6][C:7]([OH:9])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:10][O:11][C:12](=[O:27])[C@H:13]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:14][C:15](=[O:19])[C@H:16]([CH3:18])[NH2:17].C(N[C@H](C(O)=O)C)(OC(C)(C)C)=O.Cl.COC(=O)[C@H](CC1C=CC=CC=1)N>>[CH3:10][O:11][C:12](=[O:27])[C@H:13]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH:14][C:15](=[O:19])[C@H:16]([CH3:18])[NH:17][C:7](=[O:9])[CH2:6][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 4

HCID 71606Cyclopentylacetic acidHCID 75736Methyl L-phenylalaninate hydrochlorideHCID 85082Tert-butoxycarbonylalanineHCID 12988705Alanylphenylalanine methyl ester

Product 1

HCID 9841827N-[N-(Cyclopentylacetyl)-L-alaninyl]-L-phenylalanine Methyl Ester

Procedure

Following General Procedure U and using cyclopentylacetic 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=137-139° C.). The reaction was monitored by tlc (Rf=0.23 in 1:1 EtOAc/hexanes).

Workup

  1. customprepared
  2. customfollowed by removal of the BOC-group
  3. customwas prepared as a solid (mp=137-139° C.)

Sources & evidence

ORD record
ord-92a202bb77d9478f9b04e14a17635634
Source dataset
uspto-grants-2005_05
Patent number
US06888022B2

Reaction notes

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