Water → 2-[(1R)-1-aminoethyl]-1-(4-methylphenyl)sulfonylpyrrole-3-carboxylic acid;2,2,2-trifluoroacetic acid

HRID 1055816Notes

Reaction equation

HRID 1055816 reaction equation
C(OC([NH:8][C@@H:9]([C:11]1[N:12]([S:23]([C:26]2[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:13]=[CH:14][C:15]=1[C:16]([O:18]C(C)(C)C)=[O:17])[CH3:10])=O)(C)(C)C.[C:33]([OH:39])([C:35]([F:38])([F:37])[F:36])=[O:34].O>C(Cl)Cl>[F:36][C:35]([F:38])([F:37])[C:33]([OH:39])=[O:34].[NH2:8][C@@H:9]([C:11]1[N:12]([S:23]([C:26]2[CH:27]=[CH:28][C:29]([CH3:30])=[CH:31][CH:32]=2)(=[O:25])=[O:24])[CH:13]=[CH:14][C:15]=1[C:16]([OH:18])=[O:17])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 89783443(R)-tert-butyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-1-tosyl-1H-pyrrole-3-carboxylate

Product 1

HCID 1317364102-[(1R)-1-aminoethyl]-1-(4-methylphenyl)sulfonylpyrrole-3-carboxylic acid;2,2,2-trifluoroacetic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 2-(1-((tert-butoxycarbonyl)amino)ethyl)-1-tosyl-1H-pyrrole-3-carboxylate (702c; 25.11 g, 54.0 mmol) in 120 mL DCM was added TFA (Aldrich; 120 mL, 1621 mmol) slowly in portions (Caution: gas evolution was observed). After complete addition, the dark brown reaction was stirred 5 min, was fitted with a water-cooled reflux condenser and drying tube and was placed in a pre-heated 50° C. oil bath. The reaction was heated at reflux for 3 h; gas evolution was mild. The reaction was cooled and concentrated in vacuo and the solid material was dried in vacuo for 48 h to give (R)-2-(1-aminoethyl)-1-tosyl-1H-pyrrole-3-carboxylic acid compound with 2,2,2-trifluoroacetic acid (1:1) (22.83 g, 54.1 mmol, 100% yield). 1H NMR (400 MHz, MeOH-d4) d ppm 7.89 (2H, d, J=8.4 Hz), 7.57 (1H, d, J=3.5 Hz), 7.52 (2H, d, J=8.2 Hz), 6.79 (1H, d, J=3.5 Hz), 5.28 (1H, q, J=6.8 Hz), 2.47 (3H, s), 1.32 (3H, d, J=6.8 Hz). m/z (ESI, +ve) 309.0 (M+H)+.

Workup

  1. additionAfter complete addition
  2. customthe dark brown reaction
  3. temperaturecooled
  4. temperaturereflux condenser
  5. customdrying tube
  6. customwas placed in a pre-heated 50° C.
  7. temperatureThe reaction was heated
  8. temperatureat reflux for 3 h
  9. temperatureThe reaction was cooled
  10. concentrationconcentrated in vacuo
  11. customthe solid material was dried in vacuo for 48 h

Sources & evidence

ORD record
ord-3ceb1f4457d245859f5780a853ebacf4
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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