Sodium hydride → HCID 10869178, compound

HRID 1759770Notes

Reaction equation

HRID 1759770 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[N+](C1C=C(S(O[CH2:31][C@H:32]2[O:34][CH2:33]2)(=O)=O)C=CC=1)([O-])=O>CN(C)C=O>[C:3]([O:7][C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH2:31][C@H:32]2[O:34][CH2:33]2)=[CH:15][CH:16]=1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 2756771N-Boc-4-hydroxyaniline

Product 1

HCID 10869178HCID 10869178, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an 8 ml dimethylformamide suspension of 60 mg of sodium hydride was added, under ice cooling, 300 mg of 4-(tert-butoxycarbonylamino)phenol. The resultant mixture was stirred at room temperature for 1 hour. Under ice cooling, 372 mg of (S)-glycidyl 3-nitrobenzenesulfonate was gradually added, then the resultant mixture was stirred at room temperature for 2 hours. The reaction was quenched with a 5 ml of saturated aqueous ammonium chloride solution, then the product was extracted with ether. The extract was washed with saturated saline, dried, filtered, then concentrated under reduced pressure to give a residue, which was then purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the above-referenced compound (9) in an amount of 315 mg (yield 83%).

Workup

  1. additionwas added, under ice cooling
  2. customThe reaction was quenched with a 5 ml of saturated aqueous ammonium chloride solution
  3. extractionthe product was extracted with ether
  4. washThe extract was washed with saturated saline
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a residue, which
  9. customwas then purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-11482ea10620409da69efe96b5dad940
Source dataset
uspto-grants-2005_01
Patent number
US06838470B2

Reaction notes

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