Hydrochloric Acid → HCID 25017316, compound

HRID 1944507Notes

Reaction equation

HRID 1944507 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:13]3[N:14]=[C:15]([CH2:18][O:19][C:20]4[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([O:28]C)=[O:27])=[C:22]([CH3:32])[CH:21]=4)[S:16][CH:17]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].[OH-].Cl.CCOC(C)=O>C1COCC1.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:13]3[N:14]=[C:15]([CH2:18][O:19][C:20]4[CH:31]=[CH:30][C:23]([O:24][CH2:25][C:26]([OH:28])=[O:27])=[C:22]([CH3:32])[CH:21]=4)[S:16][CH:17]=3)[CH:10]=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 59187449HCID 59187449, compound

Product 1

HCID 25017316HCID 25017316, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The methyl 2-(4-((4-(3-(cyclopentyloxy)phenyl)thiazol-2-yl)methoxy)-2-methylphenoxy)acetate from Step A is dissolved in 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 is 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 C1 as a white solid: 1H-NMR (400 MHz, CDCl3) δ=7.46 (s, 1H), 7.33 (m, 3H), 6.89 (m, 2H), 6.76 (dd, J=2.8, 8.8 Hz, 1H), 6.69 (d, J=8.8 Hz, 1H), 5.41 (s, 2H), 4.84 (m, 1H), 4.64 (s, 2H), 2.28 (s, 3H), 1.88 (m, 4H), 1.82 (m, 2H), 1.63 (m, 2H). MS calcd. for C24H26NO5S (M+H+) 440.2. found 440.1.

Workup

  1. washthe organic layer is washed with brine (5 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-ca6d8ca798c14e81998ad1cb9010e5af
Source dataset
uspto-grants-2013_03
Patent number
US08394841B2

Reaction notes

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