Pyridine → HCID 54138143, compound

HRID 1082167Notes

Reaction equation

[OH:1][C:2]1[C:19]2[CH2:18][S:17][CH2:16][C@@H:15]([C:20]([NH2:22])=O)[NH:14][C:13](=[O:23])[CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7](=[O:24])[C:6]=2[C:5]([CH3:25])=[C:4]([O:26][CH3:27])[CH:3]=1.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(OCC)(=O)C>O1CCOCC1>[C:20]([C@H:15]1[NH:14][C:13](=[O:23])[CH2:12][CH2:11][CH2:10][CH2:9][O:8][C:7](=[O:24])[C:6]2[C:5]([CH3:25])=[C:4]([O:26][CH3:27])[CH:3]=[C:2]([OH:1])[C:19]=2[CH2:18][S:17][CH2:16]1)#[N:22]

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 60 mg of the product of Example 68 in 1.2 ml of dioxane were added at 0° C. 36 mg of pyridine and 95 mg of trifluoroacetic acid anhydride. The mixture was allowed to warm to 20° C. within 5 min and stirring was continued for 15 min at 20° C. Ethyl acetate was added and the mixture Was washed successively with 1N hydrochloric acid, 5% sodium carbonate solution and brine. The organic layer was dried over sodium sulfate and the solvent was evaporated in vacuo. The solid residue was purified by chromatography on silica gel using hexane/ethyl acetate (1:2, v/v) as eluent, to yield 21 mg of (R)-4-cyano-16-hydroxy-14-methoxy-13-methyl-1,3,4,5,6,7,8,9,10,12-decahydro-11,2,5-benzoxathiaazacyclotetradecin-6,12-dione as a white solid.

Workup

washthe mixture Was washed successively with 1N hydrochloric acid, 5% sodium carbonate solution and brine
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent was evaporated in vacuo
customThe solid residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-d923f7d2c2624aeda50f856d6ab9f61f
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05589473

Reaction notes

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