Hydrochloric Acid → HCID 54041549, compound

HRID 2299556Notes

Reaction equation

HRID 2299556 reaction equation
ClC1SC2C=CC=CC=2N=1.N[C@H](C(O)=O)C.[S:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=[C:18]1[NH:26][C@H:27]([C:29]([OH:31])=O)[CH3:28].Cl.[CH3:33][O:34][C:35](=[O:42])[C@H:36]([CH2:38][CH2:39][CH2:40][CH3:41])[NH2:37].Cl>>[CH3:33][O:34][C:35](=[O:42])[C@@H:36]([NH:37][C:29](=[O:31])[C@H:27]([CH3:28])[NH:26][C:18]1[S:17][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=1)[CH2:38][CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 5950L-AlanineHCID 119872-ChlorobenzothiazoleHCID 7130857HCID 7130857, compoundHCID 14039065methyl (2S)-2-aminohexanoate hydrochloride

Product 1

HCID 54041549HCID 54041549, compound

Procedure

Following General Procedure B and using 2-chlorobenzothiazole (Aldrich) and L-alanine (Aldrich), N-(benzothiazol-2-yl)-L-alanine was prepared. This compound was then coupled to L-norleucine methyl ester hydrochloride (Sigma) using General Procedure D (without the 1N HCl wash) to provide for the title compound as a solid (mp=99-120° C.). The latter reaction was monitored by tlc (Rf=0.42 in 1:1 EtOAc:Hexanes) and the product was purified by preparative plate chromatography using 1:1 EtOAc:Hexanes and 5:95 MeOH:dichloromethane as the eluent.

Workup

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Sources & evidence

ORD record
ord-334a41ddb2f141b3839457574eebc7b8
Source dataset
uspto-grants-2002_12
Patent number
US06495693B2

Reaction notes

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