Trifluoroacetic acid → HCID 17986359, compound

HRID 970439Notes

Reaction equation

HRID 970439 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>>[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 69334633HCID 69334633, compound

Product 1

HCID 17986359HCID 17986359, compound

Procedure

2.27 g (6.72 mmol) of [4-(3-nitro-benzoylamino)-butyl]-carbamic acid-tert-butyl ester is mixed with 9 ml of trifluoroacetic acid and stirred for 3 hours at room temperature. The batch is carefully added to 2N NaOH solution and then extracted from ethyl acetate. The combined organic phases are filtered through a Whatman filter and concentrated by evaporation. The crude product that is obtained is recrystallized from ethanol/diisopropyl ether. 519 mg (2.19 mmol, corresponding to 33% of theory) of the product is obtained.

Workup

  1. extractionextracted from ethyl acetate
  2. filtrationThe combined organic phases are filtered through a Whatman
  3. filtrationfilter
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-9308bbd32c9d42d281bd2804d6b4d8b3
Source dataset
uspto-grants-2007_12
Patent number
US07312225B2

Reaction notes

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