Sodium Hydroxide → HCID 118235638, compound

HRID 626998Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][C:11]([N:14]3[CH2:19][CH2:18][C:17]([CH3:25])([C:20]([O:22]CC)=[O:21])[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:6][N:5]2[C:26]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH:38]([F:40])[F:39])=[C:27]([CH3:29])[N:28]=[C:4]2[CH:3]=1.[OH-].[Na+:42]>C1COCC1.CO>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[N:10][C:11]([N:14]3[CH2:19][CH2:18][C:17]([CH3:25])([C:20]([O-:22])=[O:21])[CH2:16][CH2:15]3)=[N:12][CH:13]=2)=[CH:6][N:5]2[C:26]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=3[O:37][CH:38]([F:40])[F:39])=[C:27]([CH3:29])[N:28]=[C:4]2[CH:3]=1.[Na+:42]

Participants

Conditions

Temperature: 55 °C

Procedure

To a suspension of Example 297 (0.40 g, 0.71 mmol) in THF (4 mL) and methanol (4 mL) was added 1M aqueous sodium hydroxide solution (0.67 mL, 0.68 mmol), and the mixture was heated at 55° C. The mixture was stirred at room temperature overnight. The mixture was concentrated in vacuo to remove the organic solvents and the residue was treated with diethyl ether (50 mL). The ether was decanted and the aqueous layer was diluted with water, then freeze dried, to give the title compound (0.39 g, 97%) as an off-white solid. δH 1.07 (s, 3H), 1.22 (m, 2H), 2.02 (m, 2H), 2.28 (m, 2H), 2.35 (s, 3H), 4.29 (m, 4H), 6.99 (m, 1H), 7.14 (m, 2H), 7.24 (s, 1H), 7.30 (m, 2H), 7.49 (s, 1H), 7.75 (d, J 0.2 Hz, 1H), 8.30 (s, 1H), 8.36 (s, 2H). LCMS (pH 3): MH+ 540.0, RT 2.02 minutes. LCMS (pH 10): MH+ 540.0, RT 1.69 minutes.

Workup

concentrationThe mixture was concentrated in vacuo
customto remove the organic solvents
additionthe residue was treated with diethyl ether (50 mL)
customThe ether was decanted
additionthe aqueous layer was diluted with water
customfreeze dried

Sources & evidence

ORD record: ord-e0b74a9d11e847538765123b83da9150
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309243B2

Reaction notes

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