Sodium hydride → HCID 69527401, compound

HRID 1822810Notes

Reaction equation

HRID 1822810 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:19])[NH:9][CH2:10][CH2:11][CH2:12][C:13](=[O:18])[NH:14][CH2:15][C:16]#[CH:17])([CH3:6])([CH3:5])[CH3:4].[Cl-].[NH4+]>CS(C)=O>[C:3]([O:7][C:8](=[O:19])[NH:9][CH2:10][CH2:11][CH2:12][C:13]1[O:18][C:16]([CH3:17])=[CH:15][N:14]=1)([CH3:5])([CH3:4])[CH3:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 13561207HCID 13561207, compound

Product 1

HCID 69527401HCID 69527401, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium hydride (60 mg, 60% dispersion) was added to a mixture of (3-prop-2-ynylcarbamoylpropyl)carbamic acid tert-butyl ester (0.5 g) and dimethylsulfoxide (10 mL) under argon. The mixture was stirred at rt for 4 h. Saturated aqueous ammonium chloride (30 mL) was added to quench the reaction and the mixture was extracted with ethyl acetate (2×). Combined ethyl acetate layers were washed with water (1×), dried over sodium sulfate, filtered and evaporated. The crude product was purified by column chromatography (20 to 30% ethyl acetate in hexanes) to give [3-(5-methyloxazol-2-yl)-propyl]carbamic acid tert-butyl ester (150 mg). HCl in dioxane (4M, 3 mL) was added to [3-(5-methyl-oxazol-2-yl)-propyl]-carbamic acid tert-butyl ester (250 mg). The mixture was stirred at rt for 2 h and was evaporated to dryness in vacuo to give the HCl salt of 3-(5-Methyloxazol-2-yl)propylamine (228 mg). ESI-MS (m/z) 141 [M+H]+.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate (2×)
  4. washCombined ethyl acetate layers were washed with water (1×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by column chromatography (20 to 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8accb5bbb0fe4cb392cd27cc948be17d
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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