Ethyl acetate hexane → HCID 57310181, compound

HRID 1385761Notes

Reaction equation

HRID 1385761 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:16])[C@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:17][O:18][C@H:19]([CH2:23][CH2:24][C@H:25]([O:29][CH3:30])[C:26]([OH:28])=O)[C:20]([OH:22])=O.[CH3:31][CH2:32][O:33][C:34]([CH3:36])=[O:35].C[CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>CO.CCOC(C)=O>[CH2:2]([O:9][C:10]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:20](=[O:22])[C@H:19]([O:18][CH3:17])[CH2:23][CH2:24][C@H:25]([O:29][CH3:30])[C:26]([N:12]1[CH2:11][CH2:15][CH2:14][C@@H:36]1[C:34]([O:33][CH2:32][C:31]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:35])=[O:28])=[O:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 22827650benzyl (2R)-pyrrolidine-2-carboxylate hydrochlorideHCID 57234791erythro-Hexaric acid, 3,4-dideoxy-2,5-di-O-methyl-

Product 1

HCID 57310181HCID 57310181, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

Using General Procedure A with 1.51 g (6.2 mmol) D-Proline benzyl ester hydrochloride and 643 mg (3.1 mmol) (2R,5S)-2,5Dimethoxy-hexanedioic acid afforded, after flash chromatography (gradient: 10-100% EtOAc/hexane then 10% MeOH/EtOAc), 643 mg (36%) of the title compound as a yellow oil. MS m/e (%): 581 (M+H+, 100).

Workup

  1. customafforded

Sources & evidence

ORD record
ord-4320bc1263b44fbe8b5892a2aeb6c6fb
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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