Sodium hydride → HCID 117871254, compound

HRID 627027Notes

Reaction equation

HRID 627027 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH3:16])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:20][CH2:21][O:22][CH3:23]>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]([CH2:20][CH2:21][O:22][CH3:23])[C@@H:12]([CH3:16])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 736104N-carbobenzyloxyalanine

Product 1

HCID 117871254HCID 117871254, compoundYield 11.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 100 mL round-bottomed flask, (S)-2-(benzyloxycarbonylamino) propanoic acid (1 g, 4.48 mmol, Eq: 1.00) was combined with DMF (9 mL) to give a colorless solution. Sodium hydride (394 mg, 9.86 mmol, Eq: 2.2) was added. After 30 min, 1-bromo-2-methoxyethane (747 mg, 505 μL, 5.38 mmol, Eq: 1.2) was added and the reaction was stirred at rt overnight. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with water and brine then dried over Na2SO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 40 g, 0% to 10% MeOH in DCM) to give (S)-2-[benzyloxycarbonyl-(2-methoxy-ethyl)-amino]-propionic acid (0.15 g).

Workup

  1. customto give a colorless solution
  2. customThe reaction was quenched with saturated aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialthen dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (silica gel, 40 g, 0% to 10% MeOH in DCM)

Sources & evidence

ORD record
ord-73eb827742044fa5bfcff24edf2f9f79
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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