Sodium Hydroxide → HCID 57947899, compound

HRID 340983Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of S)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4,4-dimethyl-5-(phosphonooxy)pentyl 6-fluoroisoquinolin-3-ylcarbamate (340 mg, 0.55 mmol) in MeOH (30 mL) was added NaOH (0.1 N, 10.8 mL, 1.08 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 10 min and concentrated. The residue was dissolved in small amount of water and lyophilized to give sodium (S)-4-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-5-(6-fluoroisoquinolin-3-ylcarbamoyloxy)-2,2-dimethylpentyl phosphate (343 mg, 94.1%) as white solid. LRMS (M−2Na++3H+) m/z 615.5.

Workup

concentrationconcentrated
dissolutionThe residue was dissolved in small amount of water

Sources & evidence

ORD record: ord-967d81149e7c4671b812407606c4ac2e
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895582B2

Reaction notes

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