Hydrochloric Acid → HCID 58012093, compound

HRID 660910Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:18])[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[NH:7][C:6]1=[O:17].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:26]1([CH3:29])[CH2:28][CH2:27]1.Cl>CC(C)=O.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:18])[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[N:7]([CH2:29][CH:26]2[CH2:28][CH2:27]2)[C:6]1=[O:17]

Participants

Conditions

Temperature: 50 °C

Procedure

300 mg (1.13 mmol) of the compound from Example 232A together with 1.10 g (3.38 mmol) of caesium carbonate are placed in 12 ml acetone and treated with 456 mg (3.38 mmol) of bromo-methylcyclopropane. This is stirred for 2 hrs at 50° C. The reaction mixture is then diluted with 10 ml each of ethyl acetate and water and acidified with 1 N hydrochloric acid. The phases are separated and the aqueous phase is once again extracted with 10 ml ethyl acetate. The combined organic phases are dried over sodium sulphate, filtered and concentrated in vacuo. Further purification is effected by preparative HPLC [Method 10]. 60 mg (17% of theory) of the target compound are thus obtained.

Workup

customThe phases are separated
extractionthe aqueous phase is once again extracted with 10 ml ethyl acetate
dry with materialThe combined organic phases are dried over sodium sulphate
filtrationfiltered
concentrationconcentrated in vacuo
customFurther purification
custom60 mg (17% of theory) of the target compound are thus obtained

Sources & evidence

ORD record: ord-a3356781a4db4369ac38d105ea11161e
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084481B2

Reaction notes

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