Hydrochloric Acid → HCID 57657905, compound

HRID 391608Notes

Reaction equation

[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([C:16]#[C:17][C:18]3[CH:19]=[C:20]([C:24]([N:26]=[S@:27]([CH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41]C)=[O:40])([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:28])=[O:25])[CH:21]=[N:22][CH:23]=3)[CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][C:4]([CH3:43])=[N:3]1.[OH-].[Na+].Cl>C1COCC1>[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([C:16]#[C:17][C:18]3[CH:19]=[C:20]([C:24]([N:26]=[S@:27]([CH2:35][CH2:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40])([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:28])=[O:25])[CH:21]=[N:22][CH:23]=3)[CH:13]=[CH:14][CH:15]=2)=[O:8])=[CH:5][C:4]([CH3:43])=[N:3]1

Participants

Conditions

Temperature: 0 °C

Procedure

To the solution of (S)-Methyl 5-[N-({5-[(3-{[(1,3-dimethyl-1H-pyrazol-5-yl)carbonyl]amino}phenyl)ethynyl]pyridin-3-yl}carbonyl)-S-phenylsulfonimidoyl]pentanoate (120 mg, 0.2 mmol) in THF (4 mL) at 0° C. was added dropwise a solution of aqueous NaOH (0.5 N, 2.0 mL). After the reaction mixture was stirred at 0° C. for 2 hours, 2 N HCl was carefully added to adjust the pH ˜5 followed by a partition between aqueous NH4Cl and EtOAc. The EtOAc layer was further washed with brine once and dried with anhydrous sodium sulfate. The organic layer was decanted, concentrated and subject to a gradient column chromatography (from EtOAc to MeOH-EtOAc 1:5) yielding the title compound as white foam in amount of (85 mg, 73%).

Workup

customa partition between aqueous NH4Cl and EtOAc
washThe EtOAc layer was further washed with brine once
dry with materialdried with anhydrous sodium sulfate
customThe organic layer was decanted
concentrationconcentrated

Sources & evidence

ORD record: ord-47235c0659bc45c4b79a0dd505c70068
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383825B2

Reaction notes

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