Methyl L-phenylalaninate hydrochloride → HCID 22895024, compound

HRID 2180819Notes

Reaction equation

HRID 2180819 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:3]=1.Cl.[CH3:13][O:14][C:15](=[O:30])[C@H:16]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:17][C:18](=[O:22])[C@H:19]([CH3:21])[NH2:20].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>[CH3:13][O:14][C:15](=[O:30])[C@H:16]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[NH:17][C:18](=[O:22])[C@H:19]([CH3:21])[NH:20][C:9](=[O:11])[CH2:8][C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 75736Methyl L-phenylalaninate hydrochlorideHCID 85082Tert-butoxycarbonylalanineHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 56593994HCID 56593994, compound

Product 1

HCID 22895024HCID 22895024, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following General Procedure C and using 3-pyridylacetic acid hydrochloride (Aldrich) 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=150-152° C.). The reaction was monitored by tlc (Rf=0.3 in 10% MeOH/CHCl3) and the product was purified by silica gel chromatography using 10% MeOH/CHCl3 as the eluent, followed by recrystallization from acetonitrile.

Workup

  1. customfollowed by removal of the BOC-group
  2. customwas prepared as a solid (mp=150-152° C.)
  3. customthe product was purified by silica gel chromatography
  4. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-b73a2741b3e94c2a8fc0739d6ffb58e2
Source dataset
uspto-grants-2005_05
Patent number
US06888022B2

Reaction notes

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