HCID 66655016, compound → HCID 178516275, compound

HRID 2036244Notes

Reaction equation

HRID 2036244 reaction equation
C(OC([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[O:28][CH2:29][C:30]1[O:34][N:33]=[C:32]([O:35]CC2C=CC=CC=2)[CH:31]=1)=O)C1C=CC=CC=1>Br.C(O)(=O)C>[Cl:27][C:25]1[CH:24]=[CH:23][C:22]([O:28][CH2:29][C:30]2[O:34][N:33]=[C:32]([OH:35])[CH:31]=2)=[C:21]([CH:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:19][CH2:20][NH:11]2)[CH:26]=1

Participants

4

Reactant 1

HCID 66655016HCID 66655016, compound

Product 1

HCID 178516275HCID 178516275, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of (±)-1-[2-(3-benzyloxy-isoxazol-5-ylmethoxy)-5-chloro-phenyl]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (70 mg, 0.12 mmol, 1 eq.) in 33% hydrobromic acid in acetic acid (0.64 mL) was stirred at r.t. for 1.5 hours. The solvent was removed in vacuo. The residue, redissolved in MeCN/MeOH, was purified by prep. HPLC (column: Waters XBridge, 30×75 mm, 10 um, UV/MS, acidic conditions) and evaporated (genevac) to give (±)-5-[4-chloro-2-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-phenoxymethyl]-isoxazol-3-ol.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue, redissolved in MeCN/MeOH
  3. customwas purified by prep
  4. customHPLC (column: Waters XBridge, 30×75 mm, 10 um, UV/MS, acidic conditions) and evaporated (genevac)

Sources & evidence

ORD record
ord-a0ce73d70da74d90b205e7abddaef3e3
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

Loading…