Methyl L-phenylalaninate hydrochloride → N-[N-(Cyclohex-1-enylacety)-L-alaninyl]-L-phenylalanine Methyl Ester

HRID 322732Notes

Reaction equation

HRID 322732 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH: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][C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 4

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 85082Tert-butoxycarbonylalanineHCID 866991-Cyclohexene-1-acetic acidHCID 12988705Alanylphenylalanine methyl ester

Product 1

HCID 10177298N-[N-(Cyclohex-1-enylacety)-L-alaninyl]-L-phenylalanine Methyl Ester

Procedure

Following General Procedure U and using cyclohex-1-enylacetic acid (Alfa) 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=139-142° C.). The reaction was monitored by tlc (Rf=0.27 in 1:1 EtOAc/hexanes).

Workup

  1. customprepared
  2. customfollowed by removal of the BOC-group
  3. customwas prepared as a solid (mp=139-142° C.)

Sources & evidence

ORD record
ord-67d7751624944ef981a77693b8525266
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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