Trifluoroacetic acid → HCID 44571804, compound

HRID 640067Notes

Reaction equation

HRID 640067 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([NH:17][S:18]([C:21]2[S:22][C:23]([Cl:26])=[CH:24][CH:25]=2)(=[O:20])=[O:19])[CH2:15][OH:16])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:26][C:23]1[S:22][C:21]([S:18]([NH:17][C@@H:14]([CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:15][OH:16])(=[O:19])=[O:20])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20774775HCID 20774775, compound

Product 1

HCID 44571804HCID 44571804, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-[1-(5-chloro-thiophene-2-sulfonylamino)-2-hydroxy-ethyl]-piperidine-1-carboxylic acid tert-butyl ester (0.204 g, 0.48 mmol (see example 209)) dissolved in dichloromethane (2 mL) at 0° C. was added trifluoroacetic acid (0.5 mL). The reaction was allowed to warm to 25° C. and stir overnight. The mixture was then concentrated and dichloromethane was added and evaporated 6 times to yield a crude solid. Purification by HPLC (C-18 column, (21×75 mm) with elution system 60-100% acetonitrile-water+0.1% TFA, 20 min gradient) gave the product as an oil (0.0166 g, 11%). MS (ESI) m/z 325 ([M+H]+).

Workup

  1. concentrationThe mixture was then concentrated
  2. additiondichloromethane was added
  3. customevaporated 6 times
  4. customto yield a crude solid
  5. customPurification
  6. washby HPLC (C-18 column, (21×75 mm) with elution system 60-100% acetonitrile-water+0.1% TFA, 20 min gradient)

Sources & evidence

ORD record
ord-bbc98275f0ef4c3c8580fc0831103d27
Source dataset
uspto-grants-2010_04
Patent number
US07691884B2

Reaction notes

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