Sodium Hydroxide → HCID 86690950, compound

HRID 714744Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]3[CH:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:37])([F:36])[F:35])[C:25]([C:38]([O:40]C)=[O:39])=[CH:24][CH:23]=3)[N:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:16])([F:17])[F:18])[C:11](=[O:20])[N:10]([CH2:21][C:22]3[CH:27]=[C:26]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:36])([F:37])[F:35])[C:25]([C:38]([OH:40])=[O:39])=[CH:24][CH:23]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

215 mg (0.36 mmol) of the compound from Example 139 were dissolved in 3 ml of THF and 3 ml of methanol, and 0.36 ml of 2 N aqueous sodium hydroxide solution was added. The mixture was stirred at 80° C. for 16 h. For work-up, the mixture was diluted with 10 ml of water and extracted twice with in each case 10 ml of ethyl acetate. The aqueous phase was acidified with 1 N hydrochloric acid and once more extracted with 10 ml of ethyl acetate. The organic phases were combined, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was dried under high vacuum. This gave 222 mg (quant.) of the target compound.

Workup

extractionextracted twice with in each case 10 ml of ethyl acetate
extractiononce more extracted with 10 ml of ethyl acetate
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was dried under high vacuum

Sources & evidence

ORD record: ord-1cfea43cbec14db3a688659ee491c344
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187466B2

Reaction notes

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