Sodium hydride → HCID 117871199, compound

HRID 627026Notes

Reaction equation

HRID 627026 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+].CS(O[CH2:24][CH2:25][S:26]([CH3:29])(=[O:28])=[O:27])(=O)=O>C1COCC1>[CH2:1]([O:8][C:9]([N:11]([CH2:24][CH2:25][S:26]([CH3:29])(=[O:28])=[O:27])[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 736104N-carbobenzyloxyalanineHCID 184645972-(Methylsulfonyl)ethyl methanesulfonate

Product 1

HCID 117871199HCID 117871199, compoundYield 41.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 100 mL round-bottomed flask, (S)-2-(benzyloxycarbonylamino)propanoic acid (331 mg, 1.48 mmol, Eq: 1.00) was combined with THF (9 mL) to give a colorless solution. Sodium hydride (131 mg, 3.26 mmol, Eq: 2.2) was added. The reaction was stirred at rt for 30 min, then 2-(methylsulfonyl)ethyl methanesulfonate (300 mg, 1.48 mmol, Eq: 1.00) 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, 10% to 60% EtOAc in hexanes) to give (S)-2-[benzyloxycarbonyl-(2-methanesulfonyl-ethyl)-amino]-propionic acid (201 mg).

Workup

  1. customto give a colorless solution
  2. stirringthe reaction was stirred at rt overnight
  3. customThe reaction was quenched with saturated aqueous NH4Cl
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialthen dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified by flash chromatography (silica gel, 40 g, 10% to 60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-38185ec196f44befa7d7885b6a987231
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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