methyl (2S)-2-aminohexanoate hydrochloride → HCID 54529792, compound

HRID 2299555Notes

Reaction equation

HRID 2299555 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][CH:12]([C:14]([OH:16])=O)[CH3:13])[CH:2]=1.Cl.[CH3:18][O:19][C:20](=[O:27])[C@H:21]([CH2:23][CH2:24][CH2:25][CH3:26])[NH2:22]>>[CH3:18][O:19][C:20](=[O:27])[C@@H:21]([NH:22][C:14](=[O:16])[CH:12]([CH3:13])[NH:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

3

Reactant 2

HCID 14039065methyl (2S)-2-aminohexanoate hydrochlorideHCID 18380282HCID 18380282, compound

Product 1

HCID 54529792HCID 54529792, compound

Procedure

Using General Procedure G, followed by hydrolysis set forth in General Procedure C, N-(quinolin-3-yl)-D,L-alanine was prepared. This compound was then coupled to L-norleucine methyl ester hydrochloride (Sigma) using General Procedure D to provide for the title compound as an oil. The latter reaction was monitored by tlc (Rf=0.76 in 10% methanol/methylene chloride and 0.07 in 1:1 EtOAc:Hexanes and the product was purified by flash chromatography using 10% methanol/methylene chloride as the eluent.

Workup

  1. customfollowed by hydrolysis
  2. customwas prepared

Sources & evidence

ORD record
ord-0d08bd304c224a0ba8e9d4551e692592
Source dataset
uspto-grants-2002_12
Patent number
US06495693B2

Reaction notes

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