Proton sponge → HCID 68713421, compound

HRID 1818819Notes

Reaction equation

HRID 1818819 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][CH2:18][CH:19]([OH:23])[CH2:20][NH:21][CH3:22])[S:9]1(=[O:25])=[O:24].[C:26]([O:30][C:31](=[O:33])[NH2:32])([CH3:29])([CH3:28])[CH3:27].F[B-](F)(F)F.C[O+](C)C.CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][CH2:18][C@H:19]([O:23][CH3:26])[CH2:20][NH:21][CH3:22])[S:9]1(=[O:25])=[O:24].[C:26]([O:30][C:31](=[O:33])[NH2:32])([CH3:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 88675Proton spongeHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 68711549HCID 68711549, compound

Product 1

HCID 68713421HCID 68713421, compoundYield 162.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-1-(methylamino)butan-2-ol-carbamic acid tert-butyl ester (75 mg, 0.161 mmol), trimethyloxonium tetrafluoroborate (71 mg, 0.483 mmol), proton sponge (121 mg, 0.564 mmol) and 4A molecular sieves were stirred in dichloromethane (5 mL) in a sealed vial at room temperature for 18 hr. The reaction mixture was concentrated then loaded directly onto silica gel and purified via Isco chromatography (Redisep, silica, gradient 0-50% ethyl acetate in hexane to afford 0.065 g of (2S)-4-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-2-methoxy-N-methylbutan-1-amine-carbamic acid tert-butyl ester as a clear oil. This material was dissolved in diethyl ether and methanol and 4N HCl in dioxane was added a precipitate formed. The mixture was filtered to afford 0.050 g of (2S)-4-[3-(2-fluorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-2-methoxy-N-methylbutan-1-amine as a brown solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified via Isco chromatography (Redisep, silica, gradient 0-50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3cc19ae0a815402b911ce3fd4c22872d
Source dataset
uspto-grants-2009_10
Patent number
US07601722B2

Reaction notes

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