L-Alanine → HCID 54033987, compound

HRID 1886333Notes

Reaction equation

N[C@H](C(O)=O)C.[C:7]([C@@H:10]([NH:14][C@H:15]([C:17]([OH:19])=O)[CH3:16])[CH2:11][CH2:12][CH3:13])(=[O:9])[NH2:8].Cl.[CH2:21]([O:29][C:30]([C@@H:32]1[CH:37]2[CH2:38][CH2:39][CH:34]([CH2:35][CH2:36]2)[NH:33]1)=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>>[CH2:21]([O:29][C:30]([C@@H:32]1[CH:37]2[CH2:38][CH2:39][CH:34]([CH2:35][CH2:36]2)[N:33]1[C:17](=[O:19])[C@@H:15]([NH:14][C@H:10]([C:7](=[O:9])[NH2:8])[CH2:11][CH2:12][CH3:13])[CH3:16])=[O:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

Reactant 3

HCID 5950L-Alanine

HCID 53938285HCID 53938285, compound

HCID 67917358HCID 67917358, compound

Product 1

HCID 54033987HCID 54033987, compoundYield 21%

Procedure

Using the procedure described in Example 1, but replacing (S)-N-(S)-1-(ethoxycarbonyl)butyl]alanine by (S)-N-[(S)-1-carbamoylbutyl]alanine described in stage A of Example 3, and (3S)-3-carbamoyl-2-azobicyclo[2.2.2]-octane by (3S)-2-azabicyclo[2.2.2]octane-3-carboxylic acid n-octyl ester hydrochloride obtained in stage A (neutralized beforehand with triethylamine), the expected product is obtained from the product being purified by chromatography on silica gel (elution solvent: dichloromethane/ethanol, 95:5).

Sources & evidence

ORD record: ord-d2aeaaded3d041ebbc3c3d94230d3cae
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05151432

Reaction notes

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