Hydrochloric Acid → HCID 89699899, compound

HRID 1055652Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:15])([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=[O:6].CS(O[CH:22]1[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C=O)C>[C:29]([O:28][C:26]([N:24]1[CH2:25][CH:22]([O:1][C:2]2[CH:3]=[C:4]([CH:8]=[C:9]([S:11]([F:16])([F:12])([F:13])([F:14])[F:15])[CH:10]=2)[C:5]([OH:7])=[O:6])[CH2:23]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

Conditions

Temperature: 90 °C

Procedure

100 mg (0.38 mmol) of the compound of Example 24A and 104 mg (0.42 mmol) of tert-butyl 3-[(methylsulphonyl)oxy]azetidine-1-carboxylate together with 259 mg (0.80 mmol) of caesium carbonate were initially charged in 1 ml of DMF and stirred at 90° C. overnight. The mixture was then stirred into 10 ml of 0.1 M hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC (Method 18). This gave 60 mg (88% pure, 33% of theory) of the title compound.

Workup

extractionextracted with ethyl acetate
washThe organic phase was washed with saturated sodium chloride solution
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by preparative HPLC (Method 18)

Sources & evidence

ORD record: ord-4d8441a47016452d9572787d2459c726
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394309B2

Reaction notes

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