Phosphorus pentachloride → N-[(S)-2-methylhexanoyl]-alpha-L-glutamyl-5-aminopyridine-2-carbonitrile

HRID 1614302

Reaction equation

[CH3:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[C:3](Cl)=[O:4].P(Cl)(Cl)(Cl)(Cl)Cl.C[C@@H](CCCC)C(O)=O.[NH2:25][C@H:26]([C:32]([C:34]1[C:35]([C:41]#[N:42])=[N:36][CH:37]=[C:38]([NH2:40])[CH:39]=1)=[O:33])[CH2:27][CH2:28][C:29](=[O:31])[OH:30].C([O-])(O)=O.[Na+]>O1CCCC1.O>[CH3:1][C@@H:2]([CH2:6][CH2:7][CH2:8][CH3:9])[C:3]([NH:25][C@H:26]([C:32]([C:34]1[C:35]([C:41]#[N:42])=[N:36][CH:37]=[C:38]([NH2:40])[CH:39]=1)=[O:33])[CH2:27][CH2:28][C:29](=[O:30])[OH:31])=[O:4]

Participants

Conditions

Temperature: 20 °C

Procedure

To prepare this compound, a solution of 1.2 g (0.008 mol) of (S)-2-methylhexanoyl chloride (prepared by reacting phosphorus pentachloride with (S)-2-methylhexanoic acid, itself obtained by the method described in J. Biol. Chem. 1926, 70, 211; ibid, 1932, 98, 1 and Chem. Pharm. Bull. 1979, 27, 747) in 30 cm3 of anhydrous tetrahydrofuran is added dropwise to a solution of 1 g (0.004 mol) of alpha-L-glutamyl-5-aminopyridine-2-carbonitrile (prepared according to J. Med. Chem. 1973, 16, 163) and 3.4 g (0.04 mol) of NaHCO3 in 30 cm3 of water. After stirring for 15 minutes at 20° C., the tetrahydrofuran is removed under vacuum and the remaining aqueous solution is acidified to pH 2-3 with a 6N solution of HCl, affording a precipitate of 1 g of N-[(S)-2-methylhexanoyl]-alpha-L-glutamyl-5-aminopyridine-2-carbonitrile (yield 69%, melting point 146° C., in the amorphous state) after filtration and trituration in hexane.

Workup

customTo prepare this compound
customobtained by the method
customthe tetrahydrofuran is removed under vacuum

Sources & evidence

ORD record: ord-3475011ad21748c9b365f8d32d90c930
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05196540

Linked notes

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