Ethyl bromoacetate → HCID 59774577, compound

HRID 967394Notes

Reaction equation

HRID 967394 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([OH:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([O:21][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 59774551HCID 59774551, compound

Product 1

HCID 59774577HCID 59774577, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A stirring solution of 1.4 g (0.0048 mol) of 4-(3-hydroxy-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester was dissolved in THF (24 mL) was cooled to 0° C., and 0.13 g (0.0052 mol) of NaH was added. After 30 min, 0.8 g (0.0052 mol) of ethyl bromoacetate was added, and reaction was allowed to warm to room temperature and stirred overnight. Saturated NaHCO3 (20 mL) was added and the reaction mixture was partitioned between EtOAc (200 mL) and saturated NaHCO3 (75 mL). The organic layer was washed with water (50 mL) and NaCl (50 mL), dried over Na2SO4, and concentrated to afford 0.9 g (49%) of a white powder. MS (electrospray): exact mass calculated for C19H29N3O5, 379.21. m/z found, 380.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.74 (d, J=5.3 Hz, 1H), 6.76 (d, J=7.8 Hz, 1H), 6.46 (dd, J=7.8 Hz, 5.3 Hz, 1H), 5.05 (d, J=7.33 Hz, 1H), 4.59 (s, 2H), 4.26 (q, J=7.3 Hz, 2H), 4.18-3.92 (m, 3H), 2.97 (t, J=11.6 Hz, 2H), 2.06 (d, J=12.1 Hz, 2H), 1.46 (s, 9H), 1.46-1.34 (m, 2H) 1.29 (t, J=7.3 Hz, 3H).

Workup

  1. customreaction
  2. temperatureto warm to room temperature
  3. customthe reaction mixture was partitioned between EtOAc (200 mL) and saturated NaHCO3 (75 mL)
  4. washThe organic layer was washed with water (50 mL) and NaCl (50 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-afcc5819d0284ad0bbff71f15c08eb10
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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