HCID 69287986, compound → HCID 69289214, compound

HRID 2375786Notes

Reaction equation

HRID 2375786 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:11][C:12]2[CH:16]=[C:15]([C:17]3[S:18][C:19]([Cl:22])=[CH:20][CH:21]=3)[O:14][N:13]=2)[CH:8]=[CH:9][CH:10]=1)=[O:5])C>CO.C1COCC1.O>[Cl:22][C:19]1[S:18][C:17]([C:15]2[O:14][N:13]=[C:12]([CH2:11][N:7]3[CH:8]=[CH:9][CH:10]=[C:6]3[C:4]([OH:5])=[O:3])[CH:16]=2)=[CH:21][CH:20]=1

Participants

3

Reactant 1

HCID 69287986HCID 69287986, compound

Product 1

HCID 69289214HCID 69289214, compoundYield 119.6%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrrole-2-carboxylic acid ethyl ester (135 mg) in MeOH/THF/H2O (3:1:1, 5 mL) was added LiOH monohydrate (100 mg). The mixture was refluxed for 2 h after which it was cooled to RT and concentrated. The mixture was acidified by the addition of 1 N aqueous KHSO4 solution and extracted with ethyl acetate. The combined organic phases were dried (MgSO4) and concentrated in vacuo to provide crude 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrrole-2-carboxylic acid (148 mg) which was directly used in the next step. MS (ESI−): m/e=307 [M−H]−, chloro pattern.

Workup

  1. temperatureThe mixture was refluxed for 2 h after which it
  2. concentrationconcentrated
  3. additionThe mixture was acidified by the addition of 1 N aqueous KHSO4 solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82f655a008fe4b488e3799056078b1ce
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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