Hydrochloric Acid → (R)-3-(5-amino-2-fluoro-phenyl)-3-methyl-[1,4]oxazepan-5-one hydrochloride

HRID 1186186Notes

Reaction equation

HRID 1186186 reaction equation
C(=[N:14][C:15]1[CH:16]=[CH:17][C:18]([F:30])=[C:19]([C@@:21]2([CH3:29])[NH:27][C:26](=[O:28])[CH2:25][CH2:24][O:23][CH2:22]2)[CH:20]=1)(C1C=CC=CC=1)C1C=CC=CC=1.[ClH:31]>O1CCOCC1>[ClH:31].[NH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:30])=[C:19]([C@@:21]2([CH3:29])[NH:27][C:26](=[O:28])[CH2:25][CH2:24][O:23][CH2:22]2)[CH:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58563044(R)-3-[5-(Benzhydrylidene-amino)-2-fluoro-phenyl]-3-methyl-[1,4]oxazepan-5-one

Product 1

HCID 67468567(R)-3-(5-amino-2-fluoro-phenyl)-3-methyl-[1,4]oxazepan-5-one hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (R)-3-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-3-methyl-[1,4]oxazepan-5-one (338 mg, 0.84 mmol) in dioxane (5 ml) was treated with hydrochloric acid (1 N, 1.01 ml) at room temperature for 16 hours. For the workup, the reaction mixture was evaporated at reduced pressure, the resulting residue suspended in hydrochloric acid (1 N, 3 ml) and extracted with diethylether (2×10 ml). The combined organic layers were washed again with hydrochloric acid (1 N, 3 ml), then the aqueous layers were combined and evaporated at reduced pressure to yield the (R)-3-(5-amino-2-fluoro-phenyl)-3-methyl-[1,4]oxazepan-5-one hydrochloride (intermediate C13A) as a light brown foam (225 mg, 97% of theory) which was engaged in the next step without further purification. MS (ISP): m/z=239.3 [M+H]+.

Workup

  1. customFor the workup, the reaction mixture was evaporated at reduced pressure
  2. extractionextracted with diethylether (2×10 ml)
  3. washThe combined organic layers were washed again with hydrochloric acid (1 N, 3 ml)
  4. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-e2ca9821e2744692896b7dce0bda6013
Source dataset
uspto-grants-2014_03
Patent number
US08673894B2

Reaction notes

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