Triethylamine → Nipecotic Acid

HRID 1737923Notes

Reaction equation

HRID 1737923 reaction equation
C1[C:5]2([CH2:10][CH2:9][N:8](C(=O)[C@H](NC(=O)C3C=C(Cl)C=C(Cl)C=3)CCC(O)=O)[CH2:7][CH2:6]2)CCC1.Cl[C:31]([O:33]CC)=[O:32].C(N(CC)CC)C>C1COCC1>[NH:8]1[CH2:7][CH2:6][CH2:5][CH:10]([C:31]([OH:33])=[O:32])[CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 65987Spiroglumide

Product 1

HCID 4498Nipecotic AcidYield 123.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method described in Example 1 was again used in this case, first of all by reacting 60 g (0.136 moles) of (R)-5-(8-azaspiro[4.5]decan-8-yl)-4-(3,5-dichloro-benzoylamino)-5-oxopentanoic acid (CR 2194) with 14 ml of ethyl chloroformate (0.1469 moles) in the presence of 20 ml of triethylamine (0.1435 moles) in THF and then by reacting the mixed anhydride thus formed with 19.2 g (0.1685 moles) of piperidine-3-carboxylic acid dissolved in THF/H2O. Upon completion of the reaction the reaction mixture was treated as described in Example 1. The crude oily residue thus obtained was precipitated by treatment with ligroin. The crude product was crystallized by acetonitrile. After cooling, the precipitate was filtered and dried at 60° C. under vacuum, producing 47.3 g (0.086 moles) of the pure product with a yield of 63% (C27H35Cl2N3O5).

Sources & evidence

ORD record
ord-4f6237fc55974946a31984cf7106aef9
Source dataset
uspto-grants-1999_10
Patent number
US05962502

Reaction notes

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