Sodium Hydroxide → HCID 57947681, compound

HRID 341016Notes

Reaction equation

[C:1]1([C:7]2[CH:11]=[C:10]([NH:12][C:13](=[O:40])[O:14][CH2:15][C@@H:16]([N:26]([CH3:39])[C:27]([NH:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:32]=3[Cl:38])=[O:28])[CH2:17][C@@H:18]([OH:25])[CH2:19][O:20][P:21]([OH:24])([OH:23])=[O:22])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+:42]>>[P:21]([O-:24])([O-:23])([O:20][CH2:19][C@H:18]([OH:25])[CH2:17][C@H:16]([N:26]([CH3:39])[C:27]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:32]=1[Cl:38])=[O:28])[CH2:15][O:14][C:13](=[O:40])[NH:12][C:10]1[O:9][N:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:11]=1)=[O:22].[Na+:42].[Na+:42]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 57947401HCID 57947401, compound

Product 1

HCID 57947681HCID 57947681, compound

Procedure

To a mixture of (2S,4R)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4-hydroxy-5-(phosphonooxy)pentyl 3-phenylisoxazol-5-ylcarbamate (48 mg, 0.08 mmol, 1.0 equiv.) at 0° C., was added NaOH (0.1 N, 1.6 mL, 2.0 equiv.) dropwise. The mixture was stirred at RT for 1 h followed by concentration to give sodium (2R,4S)-4-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-2-hydroxy-5-(3-phenylisoxazol-5-ylcarbamoyloxy)pentyl phosphate (55 mg, quant.) as a white solid. LRMS (M−2Na+ 3H+) m/z 601.5.

Workup

concentrationfollowed by concentration

Sources & evidence

ORD record: ord-bc71525bfc174b7daec0d9780ab3dad1
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895582B2

Reaction notes

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