Isovaleric Acid → HCID 22895037, compound

HRID 2180809Notes

Reaction equation

HRID 2180809 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH:3]([CH3:5])[CH3:4].Cl.[CH2:9]([O:13][C:14](=[O:29])[C@H:15]([CH3:28])[NH:16][C:17](=[O:27])[C@H:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[NH2:19])[CH:10]([CH3:12])[CH3:11].C(N[C@H](C(O)=O)CC1C=CC=CC=1)(OC(C)(C)C)=O.Cl.C(OC(=O)[C@H](C)N)C(C)C>CO.C(Cl)(Cl)Cl>[CH2:9]([O:13][C:14](=[O:29])[C@H:15]([CH3:28])[NH:16][C:17](=[O:27])[C@H:18]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH:19][C:1](=[O:7])[CH2:2][CH:3]([CH3:5])[CH3:4])[CH:10]([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 10430Isovaleric AcidHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 69622900HCID 69622900, compoundHCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Product 1

HCID 22895037HCID 22895037, compound

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Following General Procedure C and using isovaleric acid (Aldrich) and N-(L-phenylalaninyl)-L-alanine iso-butyl ester hydrochloride (prepared from N-BOC-L-phenylalanine (Sigma) and L-alanine iso-butyl ester hydrochloride (prepared as described in Example 83A 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=135-138° C.). The reaction was monitored by tlc (Rf=0.3 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=135-138° C.)
  3. customthe product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6db2fb0da0694910a4fd2762d4e246a4
Source dataset
uspto-grants-2005_05
Patent number
US06888022B2

Reaction notes

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