Lithium Hydroxide → HCID 44600327, compound

HRID 1177602Notes

Reaction equation

HRID 1177602 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][O:27][CH2:28][C:29]([O:31]C)=[O:30])[CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18]1)[N:11]=2.[OH-].[Li+]>C1COCC1.O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][CH:13]=[C:12]([C:17]1([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:18][CH2:19]1)[N:11]=2)[CH2:26][O:27][CH2:28][C:29]([OH:31])=[O:30]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67111911HCID 67111911, compound

Product 1

HCID 44600327HCID 44600327, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenyl)methoxy)acetate (0.040 g, 0.089 mmol) in THF (2.00 mL) was added a solution of lithium hydroxide (0.011 g, 0.45 mmol) in 1.0 mL of water. The reaction mixture was stirred for 10 min. The THF was removed, and the reaction mixture acidified to pH 1 with 5N HCl. The resulting solid was rinsed with water and diethyl ether, and the solid was dried in vacuo at 50° C. for 2 h to give 2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)benzyloxy)acetic acid. MS (ESI) m/z: calculated: 434.1; Observed: 435.0 (M++1).

Workup

  1. customThe THF was removed
  2. washThe resulting solid was rinsed with water and diethyl ether
  3. customthe solid was dried in vacuo at 50° C. for 2 h

Sources & evidence

ORD record
ord-4965cffc937a463889d1503c71da1eac
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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