Water → 3-(5-(5-(1-phenylcyclopropyl)[1,3]thiazolo[5,4-b]pyridin-2-yl)-1,3-dihydro-2H-isoindol-2-yl)propanoic acid

HRID 1177654Notes

Reaction equation

HRID 1177654 reaction equation
[C:1]1([C:7]2([C:10]3[N:15]=[C:14]4[S:16][C:17]([C:19]5[CH:20]=[C:21]6[C:25](=[CH:26][CH:27]=5)[CH2:24][N:23]([CH2:28][CH2:29][C:30]([O:32]C)=[O:31])[CH2:22]6)=[N:18][C:13]4=[CH:12][CH:11]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.O.[OH-].[Li+]>C1COCC1>[C:1]1([C:7]2([C:10]3[N:15]=[C:14]4[S:16][C:17]([C:19]5[CH:20]=[C:21]6[C:25](=[CH:26][CH:27]=5)[CH2:24][N:23]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:22]6)=[N:18][C:13]4=[CH:12][CH:11]=3)[CH2:8][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67111825Methyl 3-(5-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridin-2-yl)isoindolin-2-yl)propanoate

Product 1

HCID 591748563-(5-(5-(1-phenylcyclopropyl)[1,3]thiazolo[5,4-b]pyridin-2-yl)-1,3-dihydro-2H-isoindol-2-yl)propanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(5-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)isoindolin-2-yl)propanoate (42 mg, 0.092 mmol) was dissolved in THF (0.738 mL) and water (0.184 mL) before lithium hydroxide monohydrate (2.56 μL, 0.092 mmol) was added and stirred at ambient temperature for 2 h. The reaction mixture was concentrated, acidified with 1 N HCl, filtered, washed with water, and dried in a vacuum oven to give the title compound. MS (ESI) m/z: Calculated: 441.2; Observed: 442.2 (M++H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationfiltered
  3. washwashed with water
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-d9a2f5fe31a34733824303dccae341d3
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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