Tert-butoxycarbonylalanine → HCID 22894871, compound

HRID 322746Notes

Reaction equation

HRID 322746 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.[NH2:14][C@H:15]([C:17]([NH:19][C:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:18])[CH3:16].C(N[C@H](C(O)=O)C)(OC(C)(C)C)=O>CO.C(Cl)(Cl)Cl>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:14][C@H:15]([C:17]([NH:19][C:20]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:18])[CH3:16])=[O:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 85082Tert-butoxycarbonylalanineHCID 1454243,5-Difluorophenylacetic acidHCID 22894951HCID 22894951, compound

Product 1

HCID 22894871HCID 22894871, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following General Procedure C and using 3,5-difluorophenylacetic acid (Oakwood) and ethyl N-(L-alaninyl)-2-amino-2-phenylpropionate hydrochloride (prepared from N-BOC-L-alanine (Sigma) and D,L-α-methylphenylglycine ethyl ester (from Example D9 above) using General Procedure C, followed by removal of the BOC-group using General Procedure P), the title compound was prepared as a solid (mp=128-130° C.). The reaction was monitored by tlc (Rf=0.2 in 3% MeOH/CHCl3) and the product was purified by silica gel chromatography using 3% MeOH/CHCl3 as the eluent.

Workup

  1. customfollowed by removal of the BOC-group
  2. customwas prepared as a solid (mp=128-130° C.)
  3. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b19ed5b4e4734fc88932292879be1f5f
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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