Triethylamine → Lansoprazole

HRID 1444741Notes

Reaction equation

O.[CH3:2][C:3]1[C:4]([CH2:15][S:16][C:17]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[N:18]=2)=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([F:14])([F:13])[F:12].C(N)(N)=[O:27].OO.C(N(CC)CC)C.O.O.O.O.O.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN1CCCC1=O.O>[CH3:2][C:3]1[C:4]([CH2:15][S:16]([C:17]2[NH:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)=[O:27])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([F:13])([F:12])[F:14]

Participants

Conditions

Temperature: 2.5 °C

Procedure

(i) 40 g (0.108 mole) 2-[[[3-methyl-4-(2,2,2-trifluoro-ethoxy)-2-pyridinyl]methyl]thio]-1H-benzimidazole hydrate was dissolved in 120 ml of 1-methyl-2-pyrrolidone (NMP) at room temperature, then 0.263 g (1.077 mmole) of vanadium(V) oxytriisopropoxide were added and the reaction mixture was cooled to a temperature of from 0 to 5° C. 12.96 g (0.138 mole) of hydrogen peroxide urea adduct were suspended (optionally per partes) and the reaction was carried out at a temperature of from 0 to 10° C. for half an hour and then at a temperature of from 10 to 15° C. until the reaction was completed. At the end of the reaction, 5 ml of triethylamine and a solution of 5.68 g of sodium thiosulphate pentahydrate in 6 ml of water were added. The product was precipitated with water (280 ml at 20±5° C.) and filtered off to obtain 48.3 g of wet lansoprazole.

Workup

waitwas carried out at a temperature of from 0 to 10° C. for half an hour
customof from 10 to 15° C.
customThe product was precipitated with water (280 ml at 20±5° C.)
filtrationfiltered off

Sources & evidence

ORD record: ord-c00702bf221f4f14ace25be904d5b223
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662968B2

Reaction notes

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