Hydrochloric Acid → HCID 22504877, compound

HRID 1814179Notes

Reaction equation

HRID 1814179 reaction equation
[OH-].[Li+].C[O:4][C:5](=[O:30])[CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]3[CH:22]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)[O:20][N:19]=3)[C:9]=2[S:10][CH:11]=1.Cl>O1CCCC1.O.O>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:21]2[O:20][N:19]=[C:18]([CH2:17][O:16][C:12]3[C:9]4[S:10][CH:11]=[C:7]([CH2:6][C:5]([OH:30])=[O:4])[C:8]=4[CH:15]=[CH:14][CH:13]=3)[CH:22]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 20770869{7-[5-(4-Chloro-phenyl)-isoxazol-3-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid methyl ester

Product 1

HCID 22504877HCID 22504877, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (0.024 g, 0.58 mmol) was added to a stirred suspension of compound 77C from the preceding step (0.06 g, 0.15 mmol) in 8 mL of tetrahydrofuran/water (3:2) at room temperature. After 18 hours the resulting clear solution was diluted with 75 mL of water, stirred, and acidified with aq HCl. After −1 hour the precipitate was filtered off, rinsed 3× with water, and dried to afford 0.04 g (69% yield) of the title compound as a white solid; mp 229-230° C. (dec).

Workup

  1. filtrationAfter −1 hour the precipitate was filtered off
  2. washrinsed 3× with water
  3. customdried

Sources & evidence

ORD record
ord-ebea4f08f3cd48109ef4f11ea9933d64
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

Loading…