Lithium Hydroxide → HCID 44601109, compound

HRID 1177468Notes

Reaction equation

HRID 1177468 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:26]([NH:29][CH2:30][CH2:31][C:32]([O:34]C)=[O:33])([CH3:28])[CH3:27])[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+]>O1CCCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([C:26]([NH:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])([CH3:27])[CH3:28])[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

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67111470HCID 67111470, compound

Product 1

HCID 44601109HCID 44601109, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-(2-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)propan-2-ylamino)propanoate (0.067 g, 0.137 mmol) in tetrahydrofuran (1 mL) and methanol (0.5 mL) was added 1 M lithium hydroxide solution (0.4 mL, 0.4 mmol) and stirred at room temperature for 3 hours. The reaction mixture was concentrated in vacuo and the resulting slurry was diluted with water and neutralized (to pH=˜7) with aqueous 1 N HCl solution. The aqueous suspension was extracted with 15% MeOH/CHCl3; the organic extracts were combined, dried (K2CO3), filtered, and concentrated in vacuo to give a crude golden yellow solid (˜0.040 g). Trituration with MeOH afforded the title compound as an off-white amorphous solid. MS (ESI) m/z: Calculated: 475.5; Observed: 476.1 (M++1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe resulting slurry was diluted with water and neutralized (to pH=˜7) with aqueous 1 N HCl solution
  3. extractionThe aqueous suspension was extracted with 15% MeOH/CHCl3
  4. dry with materialdried (K2CO3)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude golden yellow solid (˜0.040 g)

Sources & evidence

ORD record
ord-dad70ee5d95548af922293458dda20f7
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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