Hydrochloric Acid → HCID 44469734, compound

HRID 38912Notes

Reaction equation

HRID 38912 reaction equation
[F:1][C:2]([F:29])([F:28])[S:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:14][CH2:13][C@H:12]([CH2:15]OS(C3C=CC(C)=CC=3)(=O)=O)[O:11][C:10]=2[CH:27]=1)(=[O:5])=[O:4].[CH2:30]([NH2:32])[CH3:31].Cl>C(#N)C>[F:1][C:2]([F:29])([F:28])[S:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:14][CH2:13][C@H:12]([CH2:15][NH:32][CH2:30][CH3:31])[O:11][C:10]=2[CH:27]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6341EthylamineHCID 86652938[(2R)-7-(Trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl 4-methylbenzenesulfonate

Product 1

HCID 44469734HCID 44469734, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation according to Example 2 using [(2R)-7-(trifluoromethylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl-4-methylbenzenesulfonate (0.27 g, 0.68 mmol), ethanamine (1 ml, 70% in water) and ACN (2 ml). Yield: 0.170 g, 76%. The amine was converted to the hydrochloric acid salt and recrystallized from acetonitrile. M.p. 208° C. MS m/z (rel. intensity, 70 eV) 325 (M+, 1) 58 (bp), 56 (8), 79 (5), 59 (4). [α]=−40° (MeOH).

Workup

  1. customPreparation
  2. customrecrystallized from acetonitrile
  3. custom[α]=−40° (MeOH)

Sources & evidence

ORD record
ord-aea087ce7a0f46a288119b28977e158b
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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