Hydrochloric Acid → HCID 69152255, compound

HRID 1744052Notes

Reaction equation

HRID 1744052 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][CH:9]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:10]([O:12]C)=[O:11])=[N:6][CH:7]=1.[Li+].[OH-].Cl>CO>[Br:1][C:2]1[CH:7]=[N:6][C:5]([NH:8][C@H:9]([C:10]([OH:12])=[O:11])[CH2:14][CH:15]([CH3:16])[CH3:17])=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 22235890HCID 22235890, compound

Product 1

HCID 69152255HCID 69152255, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 2-[(5-bromo-2-pyrimidinyl)amino]-4-methylpentanoate (1.27 g, 4.2 mmol) in MeOH (50 mL) was added an aqueous solution of LiOH (2 M, 21 mL, 42 mmol) and the reaction was stirred for 5 hours. The reaction was neutralized with aqueous 10% HCl (pH of 6–7) and concentrated to a minimum volume in vacuo. Brine was added and the product was extracted with EtOAc (3×), dried on Na2SO4, concentrated in vacuo, and stripped with MePh (3×) to afford N-(5-bromo-2-pyrimidinyl)leucine which was used as such in the next step.

Workup

  1. concentrationconcentrated to a minimum volume in vacuo
  2. additionBrine was added
  3. extractionthe product was extracted with EtOAc (3×)
  4. customdried on Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63f78c3813bd4335bdb94136ee62cd9b
Source dataset
uspto-grants-2006_03
Patent number
US07012075B2

Reaction notes

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