Hydrochloric Acid → HCID 25017317, compound

HRID 1944508Notes

Reaction equation

HRID 1944508 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH2:13][O:14][C:15]2[CH:26]=[CH:25][C:18]([O:19][CH2:20][C:21]([O:23]C)=[O:22])=[C:17]([CH3:27])[CH:16]=2)[O:11][CH:12]=1.[Li+].[OH-].Cl>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([CH2:13][O:14][C:15]2[CH:26]=[CH:25][C:18]([O:19][CH2:20][C:21]([OH:23])=[O:22])=[C:17]([CH3:27])[CH:16]=2)[O:11][CH:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59187448HCID 59187448, compound

Product 1

HCID 25017317HCID 25017317, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The solution of methyl 2-(4-((4-(2-chlorophenyl)oxazol-2-yl)methoxy)-2-methylphenoxy)acetate from Step A is diluted with THF (1 mL), then a solution of 1 M LiOH in H2O (0.2 mL) is added and the mixture is stirred for 12 h at rt. The mixture is acidified with 1 M HCl (5 mL), and extracted into EtOAc (20 mL). The organic layer is dried (MgSO4), filtered, concentrated and purified on reverse phase HPLC (H2O/MeCN gradient) to afford the title compound D1 as a white solid: 1H-NMR (400 MHz, CDCl3) δ=8.28 (s, 1H), 7.97 (dd, J=0.8, 8.0 Hz, 1H), 7.38 (dd, J=0.8, 7.6 Hz, 1H), 7.29 (t, J=7.6 Hz, 1H), 7.20 (dt, J=1.2, 7.6 Hz, 1H), 6.82 (d, J=2.4 Hz, 1H), 6.73 (dd, J=2.8, 8.8 Hz, 1H), 6.63 (d, J=8.8 Hz, 1H), 5.10 (s, 2H), 4.57 (s, 2H), 2.21 (s, 3H). MS calcd. for C19H17ClNO5 (M+H+) 374.1. found 374.1.

Workup

  1. extractionextracted into EtOAc (20 mL)
  2. dry with materialThe organic layer is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified on reverse phase HPLC (H2O/MeCN gradient)

Sources & evidence

ORD record
ord-f7f24b2dd45e445ea1790628d26e6f85
Source dataset
uspto-grants-2013_03
Patent number
US08394841B2

Reaction notes

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