Sodium Hydroxide → HCID 89544960, compound

HRID 2283431Notes

Reaction equation

HRID 2283431 reaction equation
C([O:5][C:6](=[O:31])[C:7]([CH3:30])([CH3:29])[CH2:8][NH:9][C@@H:10]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([C:20]([C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[O:21])[C:14]=1[F:28])[CH2:11][CH3:12])C(C)C.[OH-].[Na+]>C1COCC1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C@H:10]([NH:9][CH2:8][C:7]([CH3:30])([CH3:29])[C:6]([OH:31])=[O:5])[CH2:11][CH3:12])=[C:14]([F:28])[C:15]=1[C:20]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)=[O:21]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 89544779HCID 89544779, compound

Product 1

HCID 89544960HCID 89544960, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 4 A mixture of crude 3-{(R)-1-[4-Chloro-2-fluoro-3-(pyridine-3-carbonyl)-phenyl]-propylamino}-2,2-dimethyl-propionic acid isobutyl ester (assumed 1.15 mmol), NaOH (aq., 5M, 230 μL. 1.15 mmol) and THF (3 mL) was stirred at room temperature overnight. Only partial reaction. A further 1 eq. of NaOH was added, stirred for 8 h, and then another 2 eq. NaOH added and stirred overnight. LCMS: [MH]+ 393, 73%. Concentrated to give crude 3-{(R)-1-[4-Chloro-2-fluoro-3-(pyridine-3-carbonyl)-phenyl]-propylamino}-2,2-dimethyl-propionic acid and used directly in next reaction.

Workup

  1. customOnly partial reaction
  2. stirringstirred for 8 h
  3. stirringstirred overnight
  4. concentrationConcentrated

Sources & evidence

ORD record
ord-454d02f37bab4bee93aed2c8da4f36dd
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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