tert-Butyl bromoacetate → HCID 59463562, compound

HRID 1713136Notes

Reaction equation

HRID 1713136 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[N:8][CH:9]=2)[CH:4]=[C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:2]=1.Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[BH4-].[Na+]>CC#N>[C:21]([O:20][C:18](=[O:19])[CH2:17][N:8]1[CH2:9][C:10]2[N:1]=[CH:2][C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][C:5]=2[CH2:6][CH2:7]1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 4311764Sodium borohydrideHCID 56924473HCID 56924473, compound

Product 1

HCID 59463562HCID 59463562, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of ethyl 1,7-naphthyridine-3-carboxylate (905 mg, 4.476 mmol) and tert-butyl bromoacetate (1.0 g, 5.15 mmol) in CH3CN (15 mL) is refluxed overnight. Solvent is removed in vacuo and the residue is dissolve in MeOH (20 mL). To the solution is added NaBH4 (677 mg, 17.9 mmol) and the mixture is refluxed for 4 hr. The solvent is removed in vacuo and the residue is partitioned between water (30 mL) and EtOAc (30 mL). The layers are separated and the aqueous layer is extracted with EtOAc (20 ml). The combined extracts are washed with brine (20 mL), dried and evaporated. The residue is purified by flash column to give the title compound as a light yellow oil. MS (M+1): 321.2.

Workup

  1. temperatureis refluxed overnight
  2. customSolvent is removed in vacuo
  3. dissolutionthe residue is dissolve in MeOH (20 mL)
  4. temperaturethe mixture is refluxed for 4 hr
  5. customThe solvent is removed in vacuo
  6. customthe residue is partitioned between water (30 mL) and EtOAc (30 mL)
  7. customThe layers are separated
  8. extractionthe aqueous layer is extracted with EtOAc (20 ml)
  9. washThe combined extracts are washed with brine (20 mL)
  10. customdried
  11. customevaporated
  12. customThe residue is purified by flash column

Sources & evidence

ORD record
ord-d25bcdda7686476981b4fe7c0352fefa
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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