Hydrochloric Acid → HCID 70979658, compound

HRID 2271343Notes

Reaction equation

HRID 2271343 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:18]=1)[O:5][CH2:6][CH2:7][NH:8]C(=O)OC(C)(C)C.Cl.[OH-].[Na+]>CCO>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:18]=1)[O:5][CH2:6][CH2:7][NH2:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 70980523HCID 70980523, compound

Product 1

HCID 70979658HCID 70979658, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 2-[3-fluoro-5-(methylsulfonyl)phenoxy]ethyl-carbamate (1.4 g, 4.2 mmol) in EtOH (18 ml) was added HCl (1.25 M in EtOH, 6 ml). The mixture was stirred at ambient temperature for 20 h. The aqueous phase was made basic by addition of aqueous NaOH (1 M, 50 ml) and extracted with ethyl acetate (2×100 ml). The combined organic phase was washed with brine (75 ml), dried (Na2SO4) and evaporated to yield the title compound (0.77 g, 77%). MS m/z (relative intensity, 70 eV 298 (M+, 18), 296 (M+, 18), 109 (bp), 107 (99), 82 (15).

Workup

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. washThe combined organic phase was washed with brine (75 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-f10c281bdefe427d9fde890ba1716872
Source dataset
uspto-grants-2015_09
Patent number
US09120728B2

Reaction notes

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