Hydrochloric Acid → HCID 58775663, compound

HRID 1675631Notes

Reaction equation

HRID 1675631 reaction equation
CC(C)([O-])C.[Na+].[Cl:7][C:8]1[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=1[NH:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[OH:26].Br[CH2:28][C:29]([O:31]CC)=[O:30].[OH-].[Na+].Cl>C1COCC1>[Cl:7][C:8]1[CH:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=[CH:10][C:9]=1[NH:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[O:26][CH2:28][C:29]([OH:31])=[O:30]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 23676156Sodium t-butoxideHCID 66995709HCID 66995709, compound

Product 1

HCID 58775663HCID 58775663, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium tert-butoxide (0.073 g) was added to a solution of the product from step (ii) (0.2 g) in THF (10 ml) and stirred at RT for 5 min. Ethyl bromoacetate (0.078 ml) was added, the mixture stirred for 1 h before adding 2M sodium hydroxide solution (2 ml). After 3 h, 2M hydrochloric acid was added and the mixture extracted with ethyl acetate. The organics were washed with brine, dried and evaporated under reduced pressure. The residue was purified by RPHPLC, yield 0.11 g.

Workup

  1. stirringthe mixture stirred for 1 h
  2. waitAfter 3 h
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe organics were washed with brine
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was purified by RPHPLC, yield 0.11 g

Sources & evidence

ORD record
ord-44cd88b75bb64324bf2fe9bdefe9547e
Source dataset
uspto-grants-2011_08
Patent number
US08003703B2

Reaction notes

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