Hydrochloric Acid → HCID 25058550, compound

HRID 1775749Notes

Reaction equation

HRID 1775749 reaction equation
S([O:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])(C(F)(F)F)(=O)=O.[Cl-].O[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([NH3+:30])[C:26]([O:28][CH3:29])=[O:27])=[CH:20][CH:19]=1.C(N(CC)CC)C.Cl>ClCCl.O>[F:15][C:12]([F:13])([F:14])[S:9]([O:8][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C@H:25]([NH:30][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:10])=[O:8])[C:26]([O:28][CH3:29])=[O:27])=[CH:20][CH:19]=1)(=[O:10])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 110098083417-91-2

Product 1

HCID 25058550HCID 25058550, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of triflic anhydride (0.934 g, 3.3.1 mmol) in dichloromethane (3.31 mL) was added dropwise to a solution of (2S)-3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-aminium chloride (0.767 g, 3.31 mmol) and triethylamine (1.005 g, 9.93 mmol) in dichloromethane (12.79 mL) at −78° C. The mixture was stirred for 24 h at room temperature. Water (5 mL) was added and the pH was adjusted to pH=5 using 32% hydrochloric acid. The aqueous layer was extracted with diethyl ether. The organics extracts were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by column chromatography (diethyl ether) afforded the title compound as yellow solid (0.704 g, 49%).

Workup

  1. extractionThe aqueous layer was extracted with diethyl ether
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by column chromatography (diethyl ether)

Sources & evidence

ORD record
ord-46c56b76d5e94fc9ab16c281f59788c4
Source dataset
uspto-grants-2016_02
Patent number
US09260460B2

Reaction notes

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