Methyl L-phenylalaninate hydrochloride → HCID 10158080, compound

HRID 1016926Notes

Reaction equation

HRID 1016926 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.[CH3:14][O:15][C:16](=[O:31])[C@H:17]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH:18][C:19](=[O:23])[C@H:20]([CH3:22])[NH2:21].C(N[C@H](C(O)=O)C)(OC(C)(C)C)=O.Cl.COC(=O)[C@H](CC1C=CC=CC=1)N>CO.C(Cl)(Cl)Cl>[CH3:14][O:15][C:16](=[O:31])[C@H:17]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[NH:18][C:19](=[O:23])[C@H:20]([CH3:22])[NH:21][C:10](=[O:12])[CH2:9][C:4]1[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 4

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 85082Tert-butoxycarbonylalanineHCID 1454243,5-Difluorophenylacetic acidHCID 56593994HCID 56593994, compound

Product 1

HCID 10158080HCID 10158080, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following General Procedure C and using 3,5-difluorophenylacetic acid (Oakwood) and N-(L-alaninyl)-L-phenylalanine methyl ester hydrochloride (prepared from N-BOC-L-alanine (Sigma) and L-phenylalanine methyl ester hydrochloride (Sigma) using General Procedure C, followed by removal of the BOC-group using General Procedure P), the title compound was prepared as a solid (mp=173-175° C.). The reaction was monitored by tlc (Rf=0.6 in 10% MeOH/CHCl3) and the product was purified by silica gel chromatography using 4% MeOH/CHCl3 as the eluent, followed by recrystallization from 1-chlorobutane/acetonitrile.

Workup

  1. customfollowed by removal of the BOC-group
  2. customwas prepared as a solid (mp=173-175° C.)
  3. customthe product was purified by silica gel chromatography
  4. customfollowed by recrystallization from 1-chlorobutane/acetonitrile

Sources & evidence

ORD record
ord-47954f6d5ffe4d62b82793135f30cdfd
Source dataset
uspto-grants-2002_11
Patent number
US06476263B1

Reaction notes

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