Ethyl 4-piperidinecarboxylate → HCID 57595531, compound

HRID 1786027Notes

Reaction equation

HRID 1786027 reaction equation
C(OC(C1C[CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C@H:23]([N:30]([C:38](=[O:40])[CH3:39])[C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=4)[CH2:22][C@@H:21]3[CH3:41])=[O:19])=[CH:14][CH:13]=2)CC1)=O)C.[CH2:42]([O:44][C:45]([CH:47]1CCNCC1)=[O:46])C>>[C:38]([N:30]([C:31]1[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=1)[C@H:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:20]([C:18]([C:15]2[CH:14]=[CH:13][C:12]([NH:9][CH2:10][CH2:47][C:45]([OH:46])=[O:44])=[CH:17][CH:16]=2)=[O:19])[C@@H:21]([CH3:41])[CH2:22]1)(=[O:40])[CH3:39].[CH3:42][O:44][C:45](=[O:46])[CH2:47][CH2:10][NH:9][C:12]1[CH:17]=[CH:16][C:15]([C:18]([N:20]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C@H:23]([N:30]([C:38](=[O:40])[CH3:39])[C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)[CH2:22][C@@H:21]2[CH3:41])=[O:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 57595389HCID 57595389, compound

Product 2

HCID 57595531HCID 57595531, compoundHCID 68918383HCID 68918383, compound

Procedure

(2S,4R)-3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenylamino)-propionic acid was prepared following the procedure for (2S,4R)-1-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenyl)-piperidine-4-carboxylic acid ethyl ester, substituting 3-amino-propionic acid methyl ester for piperidine-4-carboxylic acid ethyl ester to yield the (2S,4R)-3-(4-{4-[Acetyl-(4-chloro-phenyl)-amino]-2-methyl-3,4-dihydro-2H-quinoline-1-carbonyl}-phenylamino)-propionic acid methyl ester. The ester was hydrolyzed to the acid by dissolving in tetrahydrofuran and ethanol and lithium hydroxide (1N) was added and heated 50° C. for 2 h. The mixture was cooled to room temperature, acidified to form a white precipitate. The solid was filtered to give to afford the product after HPLC purification.

Sources & evidence

ORD record
ord-13dcf68be0f647c1a7bb7a1010ecd46f
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

Loading…