1H-1,2,4-Triazole, 1-methyl- → HCID 67915224, compound

HRID 1030524Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[N:5][CH:4]=[N:3]1.C([Li])CCC.[C:12]([O:16][C:17]([NH:19][C@H:20]([CH:25]=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:18])([CH3:15])([CH3:14])[CH3:13].[Cl-].[NH4+]>O1CCCC1>[C:12]([O:16][C:17]([NH:19][C@@H:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[C@H:25]([C:6]1[N:2]([CH3:1])[N:3]=[CH:4][N:5]=1)[OH:26])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: -75 °C

Procedure

To a solution of 5.3 g of 1-methyl-1,2,4-triazole in 100 ml of tetrahydrofuran under nitrogen at -75° C. was added via syringe 25.6 ml of n-butyllithium. The solution was stirred 1.5 hour at -75° C. and then 6.9 g of N-tert-butoxycarbonyl-L-leucinal in 25 ml of tetrahydrofuran at -75° C. was added. The mixture was stirred 1/2 hour each at -75° C. and at -23° C. the mixture was treated with 10 ml of saturated ammonium chloride and concentrated. The residue in 100 ml of ethyl acetate was washed with 50 ml of each of water, 2N citric acid, 1M sodium bicarbonate and brine and dried. The solution was filtered and concentrated to give 8.41 g (88%) f a colorless oil which partly crystallized. Two recrystallization from iso-propyl acetate afforded 1.85 of (S)2-(tert-butoxycarbonyl)amino-4-methyl-(R)1-(1-methyl-1H-1,2,4-triazol-5 -yl)pentan-1-ol, mp 144°-145° C. [α]D26 -26±1°(c, 1.1, MeOH).

Workup

stirringThe mixture was stirred 1/2 hour each at -75° C.
concentrationconcentrated
washThe residue in 100 ml of ethyl acetate was washed with 50 ml of each of water, 2N citric acid, 1M sodium bicarbonate and brine
customdried
filtrationThe solution was filtered
concentrationconcentrated
customto give 8.41 g (88%) f a colorless oil which
custompartly crystallized
customTwo recrystallization from iso-propyl acetate

Sources & evidence

ORD record: ord-78509b585550482bb9087cf480cb7ce7
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05106835

Reaction notes

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