Tert-butoxycarbonylalanine → HCID 54504711, compound

HRID 322784Notes

Reaction equation

HRID 322784 reaction equation
[C:1]([NH:7][C@H:8]([C:13]([OH:15])=O)[C@H:9]([CH2:11][CH3:12])[CH3:10])(=[O:6])[CH2:2][CH:3]([CH3:5])[CH3:4].Cl.[CH2:17]([O:21][C:22](=[O:26])[C@H:23]([CH3:25])[NH2:24])[CH:18]([CH3:20])[CH3:19].C(N[C@H](C(O)=O)C)(OC(C)(C)C)=O>CN(C1C=CN=CC=1)C.CC(C)CO>[CH2:17]([O:21][C:22](=[O:26])[C@H:23]([CH3:25])[NH:24][C:13](=[O:15])[C@H:8]([C@H:9]([CH2:11][CH3:12])[CH3:10])[NH:7][C:1](=[O:6])[CH2:2][CH:3]([CH3:4])[CH3:5])[CH:18]([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 85082Tert-butoxycarbonylalanineHCID 29901063HCID 29901063, compoundHCID 865849812-Methylpropyl (2S)-2-aminopropanoate hydrochloride

Product 1

HCID 54504711HCID 54504711, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6560IsobutanolSolvent

Procedure

Following General Procedure C and using N-(isovaleryl)-L-isoleucine (prepared from isovaleric acid (Aldrich) and L-isoleucine methyl ester hydrochloride (Aldrich) using General Procedure C, followed by hydrolysis using General Procedure AF) and L-alanine isobutyl ester hydrochloride (prepared from N-BOC-L-alanine (Sigma) and 2-methyl-1-propanol (Aldrich) using General Procedure C (with catalystic DMAP), followed by removal of the BOC-group using General Procedure P), the title compound was prepared as a solid (mp=142-146° C.). The reaction was monitored by tlc (Rf=0.4 in 1:1 EtOAc/hexanes) and the product was purified by silica gel chromatography using 1:1 EtOAc/hexanes as the eluent to provide a 1:4 mixture of diastereomers.

Workup

  1. customfollowed by removal of the BOC-group
  2. customwas prepared as a solid (mp=142-146° C.)
  3. customthe product was purified by silica gel chromatography
  4. customto provide
  5. additiona 1:4 mixture of diastereomers

Sources & evidence

ORD record
ord-aca2a50463b3422693671269ac823a14
Source dataset
uspto-grants-2001_04
Patent number
US06211235B1

Reaction notes

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