1,4-Dioxane hydrochloride → HCID 57947550, compound

HRID 416448Notes

Reaction equation

HRID 416448 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([NH:12][C:13](=[O:39])[O:14][CH2:15][C@@H:16]([N:25]([CH3:38])[C:26]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:31]=3[Cl:37])=[O:27])[CH2:17][C@@H:18]3[CH2:22][O:21]C(C)(C)[O:19]3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.O1CCOCC1>CO>[C:1]1([C:7]2[CH:11]=[C:10]([NH:12][C:13](=[O:39])[O:14][CH2:15][C@@H:16]([N:25]([CH3:38])[C:26]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:31]=3[Cl:37])=[O:27])[CH2:17][C@@H:18]([OH:19])[CH2:22][OH:21])[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 57947818HCID 57947818, compound

Product 1

HCID 57947550HCID 57947550, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)propyl 3-phenylisoxazol-5-ylcarbamate (0.4 g, 0.7 mmol, 1.0 equiv.) in MeOH (5 mL) at 0° C., was added HCl/Dioxane (4 N, 3 mL). The mixture was warmed up to RT, stirred for 1 h, concentrated and purified on silica gel column using a mixture of DCM and MeOH to give (2S,4R)-2-(3-(2-chloro-3-fluorobenzyl)-1-methylureido)-4,5-dihydroxypentyl 3-phenylisoxazol-5-ylcarbamate (0.35 g, 96%, white solid). LRMS (M+H+) m/z 521.1.

Workup

  1. concentrationconcentrated
  2. custompurified on silica gel column
  3. additiona mixture of DCM and MeOH

Sources & evidence

ORD record
ord-0f7fbe6c7e5c477f9db96e91146754de
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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