Hydrochloric Acid → HCID 25017315, compound

HRID 1944505Notes

Reaction equation

HRID 1944505 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:10]2[N:11]=[C:12]([CH2:15][O:16][C:17]3[CH:28]=[CH:27][C:20]([O:21][CH2:22][C:23]([O:25]C)=[O:24])=[C:19]([CH3:29])[CH:18]=3)[S:13][CH:14]=2)[CH2:3][CH2:2]1.[Li+].[OH-].Cl.CCOC(C)=O>C1COCC1.O>[CH:1]1([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:10]2[N:11]=[C:12]([CH2:15][O:16][C:17]3[CH:28]=[CH:27][C:20]([O:21][CH2:22][C:23]([OH:25])=[O:24])=[C:19]([CH3:29])[CH:18]=3)[S:13][CH:14]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 59187437HCID 59187437, compound

Product 1

HCID 25017315HCID 25017315, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The solution of methyl 2-(4-((4-(2-cyclopropylphenyl)thiazol-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 3 h at rt. The mixture is acidified with 1 M HCl (0.25 mL), EtOAc (10 mL) is added and the organic layer washed with brine (5 mL). The organic layer is dried (MgSO4), filtered, concentrated and purified on reverse phase HPLC (H2O/MeCN gradient) to afford the title compound B1 as a white solid: 1H-NMR (400 MHz, CDCl3) δ=7.57 (dd, J=1.6, 7.6 Hz, 1H), 7.48 (s, 1H), 7.30 (dt, J=1.6, 7.6 Hz, 1H), 7.24 (dt, J=1.2, 7.2 Hz, 1H), 7.03 (d, J=7.6 Hz, 1H), 6.90 (d, J=2.8 Hz, 1H), 6.78 (dd, J=2.8, 8.8 Hz, 1H), 6.69 (d, J=8.8 Hz, 1H), 5.41 (s, 2H), 4.62 (s, 2H), 2.28 (s, 3H), 2.10 (m, 1H), 0.89 (m, 2H), 0.72 (m, 2H). MS calcd. for C22H22NO4S (M+H+) 396.1. found 396.1.

Workup

  1. additionis added
  2. washthe organic layer washed with brine (5 mL)
  3. dry with materialThe organic layer is dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on reverse phase HPLC (H2O/MeCN gradient)

Sources & evidence

ORD record
ord-c3cf8af565f841e7b249f23ca85808b3
Source dataset
uspto-grants-2013_03
Patent number
US08394841B2

Reaction notes

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