Sodium Hydroxide → HCID 57947954, compound

HRID 340989Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2S,4R)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4-hydroxy-5-(phosphonooxy)pentyl isoquinolin-3-ylcarbamate in MeOH (50 mL) at 0° C. was added NaOH solution (0.5 N, 16 mL, 2 equiv.) dropwise. The solution was stirred at 0° C. for 1 h and concentrated to give sodium (2R,4S)-4-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-2-hydroxy-5-(isoquinolin-3-ylcarbamoyloxy)pentyl phosphate as a white solid (quant.). The solid could be further crystallized by trituration with EtOH, followed by re-crystallization from EtOH—H2O (6:1) to give the crystalline form. LRMS (M−2Na+3H+) m/z 585.5.

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-164f0161e9314e449849f55539bf0269
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895582B2

Reaction notes

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