Phosphoric Acid → 2-(6-((5-(4-Chlorophenyl)isoxazol-3-yl)methoxy)-5-methylbenzo[b]thiophen-3-yl)acetic acid

HRID 1296070Notes

Reaction equation

HRID 1296070 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][C:5]1[C:6]2[CH:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]3[CH:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=4)[O:19][N:18]=3)=[CH:10][C:7]=2[S:8][CH:9]=1.[OH-].[K+].OP(O)(O)=O>O1CCCC1>[CH3:14][C:12]1[C:11]([O:15][CH2:16][C:17]2[CH:21]=[C:20]([C:22]3[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=3)[O:19][N:18]=2)=[CH:10][C:7]2[S:8][CH:9]=[C:5]([CH2:4][C:3]([OH:29])=[O:2])[C:6]=2[CH:13]=1

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 14797Potassium HydroxideHCID 69515759{5-Methyl-6-[5-(4-chloro-phenyl)-isoxazol-3-ylmethoxy]-benzo[b]thiophen-3-yl}-acetic acid methyl ester

Product 1

HCID 225048432-(6-((5-(4-Chlorophenyl)isoxazol-3-yl)methoxy)-5-methylbenzo[b]thiophen-3-yl)acetic acidYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 79A (0.03 g, 0.07 mmol) from the preceding step was dissolved in 2–3 mL of tetrahydrofuran, an equal volume of 2N KOH was added, and the mixture stirred at room temp. After 18 hours 75 mL of icewater was added and the mixture was acidified with H3PO4. After ˜30 min the precipitate was filtered off, rinsed 3× with water, and dried. The product was triturated in 4N HCl, allowed to stand for an hour, then filtered off, rinsed with water then ethanol, and dried to afford 0.01 g (99%) of the title compound as a white powder; mp 198–200° C. (dec). MS m/z 413 (M).

Workup

  1. additionAfter 18 hours 75 mL of icewater was added
  2. filtrationAfter ˜30 min the precipitate was filtered off
  3. washrinsed 3× with water
  4. customdried
  5. customThe product was triturated in 4N HCl
  6. waitto stand for an hour
  7. filtrationfiltered off
  8. washrinsed with water
  9. dry with materialethanol, and dried

Sources & evidence

ORD record
ord-ae02ada0128f47008b4f111ee5f9d6e6
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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