Hydrochloric Acid → HCID 89511667, compound

HRID 571258Notes

Reaction equation

HRID 571258 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:27]=[CH:26][C:16]2[N:17]([CH2:21][C:22]([O:24]C)=[O:23])[C:18](=[O:20])[O:19][C:15]=2[CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:27]=[CH:26][C:16]2[N:17]([CH2:21][C:22]([OH:24])=[O:23])[C:18](=[O:20])[O:19][C:15]=2[CH:14]=1)[S:9]([CH3:12])(=[O:10])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86681670HCID 86681670, compound

Product 1

HCID 89511667HCID 89511667, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(6-(N-(tert-butoxycarbonyl)methylsulfonamido)-2-oxobenzo[d]oxazol-3(2H)-yl)acetate (0.300 g, 0.749 mmol) in THF (5 ml), aqueous 1N LiOH (1.124 ml, 1.124 mmol) was added, and the mixture was stirred at room temperature for 30 minutes. The mixture was acidified with 1N HCl and extracted with ethyl acetate; the organic phase was washed several times with 1N HCl, dried over sodium sulfate and evaporated to dryness affording 2-(6-(N-(tert-butoxycarbonyl)-methylsulfonamido)-2-oxobenzo[d]oxazol-3(2H)-yl)acetic acid (0.234 g, 0.606 mmol, 81% yield). MS/ESI+ 386.9 [MH]+. This product was used without any further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic phase was washed several times with 1N HCl
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-da6bc5e4e32444658d65bf50f3d1faa8
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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