Sodium Hydroxide → HCID 66660124, compound

HRID 383786Notes

Reaction equation

HRID 383786 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][N:13]([C:15]2[N:20]=[C:19]([CH3:21])[CH:18]=[C:17]([NH:22][C:23]3[NH:27][N:26]=[CH:25][CH:24]=3)[N:16]=2)[CH2:12][C@@H:11]([C:28]([O:30]C)=[O:29])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[NH4+].[Cl-]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][N:13]([C:15]2[N:20]=[C:19]([CH3:21])[CH:18]=[C:17]([NH:22][C:23]3[NH:27][N:26]=[CH:25][CH:24]=3)[N:16]=2)[CH2:12][C@@H:11]([C:28]([OH:30])=[O:29])[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 66660157HCID 66660157, compound

Product 1

HCID 66660124HCID 66660124, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude carbamate was dissolved into MeOH (4 ml). 2 M aqueous solution of NaOH was added at room temperature. And the mixture was stirred at room temperature for 4 hours. After the addition of NH4Cl for neutrallization, the resulting reaction mixture was concentrated in vacuo. The residue was suspended into the mixed solvent of CHCl3/MeOH. The insoluble material was filtered off and the filtrate was concentrated again. The residue was purified with silica gel PTLC (eluent: CHCl3/MeOH=6/1) to give trans-5-[(tert-butoxycarbonyl)amino]-1-[4-methyl-6-(1H-pyrazol-5-ylamino)pyrimidin-2-yl]piperidine-3-carboxylic acid (10.9 mg) as colorless solid.

Workup

  1. customthe resulting reaction mixture
  2. concentrationwas concentrated in vacuo
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated again
  5. customThe residue was purified with silica gel PTLC (eluent: CHCl3/MeOH=6/1)

Sources & evidence

ORD record
ord-c6747fea4d794154a3b2cabd2abfe77b
Source dataset
uspto-grants-2013_02
Patent number
US08367690B2

Reaction notes

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