Sodium Hydroxide → HCID 59174855, compound

HRID 1177644Notes

Reaction equation

HRID 1177644 reaction equation
C([O:4][C@H:5]([C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[S:20][C:21]3[C:26]([N:27]=2)=[CH:25][CH:24]=[C:23]([C:28]2([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH2:30][CH2:29]2)[N:22]=3)=[C:15]([F:37])[CH:14]=1)=[O:11])[CH2:6][C:7]([OH:9])=[O:8])(=O)C.[OH-].[Na+]>C1COCC1>[F:37][C:15]1[CH:14]=[C:13]([NH:12][C:10](=[O:11])[C@@H:5]([OH:4])[CH2:6][C:7]([OH:9])=[O:8])[CH:18]=[CH:17][C:16]=1[C:19]1[S:20][C:21]2[C:26]([N:27]=1)=[CH:25][CH:24]=[C:23]([C:28]1([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:29][CH2:30]1)[N:22]=2

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 67111605HCID 67111605, compound

Product 1

HCID 59174855HCID 59174855, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3S)-3-Acetoxy-4-(3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridin-2-yl)phenylamino)-4-oxobutanoic acid (65 mg, 0.125 mmol) was dissolved in THF (1.3 mL) before 0.1 N sodium hydroxide (3.75 ml, 0.375 mmol) was added and stirred at ambient temperature for 24 h; the reaction had not gone to completion, so more NaOH was added and stirred for another 4 h. The reaction mixture was concentrated to remove the THF, acidified with 2 N HCl to crash out the product, filtered, washed with water, and dried in a vacuum oven to give the title compound. MS (ESI) m/z: Calculated: 477.1; Observed: 477.7 (M++H).

Workup

  1. additionwas added
  2. additionwas added
  3. stirringstirred for another 4 h
  4. concentrationThe reaction mixture was concentrated
  5. customto remove the THF
  6. filtrationfiltered
  7. washwashed with water
  8. customdried in a vacuum oven

Sources & evidence

ORD record
ord-68d52cf76ac14df7a7d9da8fffa251b7
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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