HCID 68741254, compound → HCID 68741878, compound

HRID 1958741Notes

Reaction equation

HRID 1958741 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[C:8]([CH2:11][C@@H:12]([NH:18][S:19]([C:22]1[S:23][C:24]([C:27]#[C:28][C:29]2[CH:30]=[C:31]([CH3:35])[CH:32]=[CH:33][CH:34]=2)=[CH:25][CH:26]=1)(=[O:21])=[O:20])[CH2:13][N+:14]([CH3:17])([CH3:16])[CH3:15])([OH:10])=[O:9]>CO.[Pd]>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[C:8]([CH2:11][C@@H:12]([NH:18][S:19]([C:22]1[S:23][C:24]([CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[CH:30]=2)=[CH:25][CH:26]=1)(=[O:20])=[O:21])[CH2:13][N+:14]([CH3:17])([CH3:15])[CH3:16])([OH:10])=[O:9]

Participants

4

Reactant 1

HCID 68741254HCID 68741254, compound

Product 1

HCID 68741878HCID 68741878, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (R)-3-carboxy-N,N,N-trimethyl-2-(5-(m-tolylethynyl)thiophene-2-sulfonamido)propan-1-aminium 2,2,2-trifluoroacetate (7 mg, 0.013 mmol) in MeOH (3 mL) was purged with nitrogen and Pd/C (10 mg) was added and the flask was purged with hydrogen and stirred for 1 h. The mixture was filtered through celite and concentrated. The residue was dissolved into H2O and lyophilized to give the title compound as a white solid (7 mg, 100%). 1H NMR (400 MHz, D2O) δ 7.42 (d, 1H, J=3.8 Hz), 7.08 (t, 1H, J=7.4 Hz), 6.97-6.94 (m, 2H), 6.88 (d, 1H, J=7.1 Hz), 6.74 (d, 1H, J=3.9 Hz) 4.14-4.11 (m, 1H), 3.52-3.49 (m, 1H), 3.46-3.44 (m, 1H), 3.15-3.07 (m, 2H), 3.10 (s, 9H), 2.84 (m, 2H) 2.32-2.25 (m, 1H) 2.15 (s, 3H), 2.01-1.96 (m, 1H); MS ESI 425.2 [M+H]+, calcd for [C20H29N2O4S2+H]+ 425.16.

Workup

  1. additionwas added
  2. customthe flask was purged with hydrogen
  3. filtrationThe mixture was filtered through celite
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved into H2O

Sources & evidence

ORD record
ord-960c94f55c1840baa39fb6ffe677d6a5
Source dataset
uspto-grants-2013_04
Patent number
US08410150B2

Reaction notes

Loading…