Hydrochloric Acid → HCID 58775663, compound

HRID 1945227Notes

Reaction equation

HRID 1945227 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 is 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 is 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-ed9c3b852c2f430c925ec71dcb024c05
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

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