Trifluoroacetic acid → HCID 22868979, compound

HRID 362229Notes

Reaction equation

HRID 362229 reaction equation
FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.[CH3:16][N:17]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:18](=[O:38])[C@@H:19]([NH:30]C(OC(C)(C)C)=O)[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1>>[CH3:16][N:17]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:18](=[O:38])[C@@H:19]([NH2:30])[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 22868973HCID 22868973, compound

Product 1

HCID 22868979HCID 22868979, compoundYield 114%

Conditions

Temperature
0 °C

Procedure

Cold trifluoroacetic acid (TFA, 4 mL) and 0.36 mL of anisole (3.28 mmol) were added to 1.215 g (2.98 mmol) of N-methyl-N-benzyl-2-(S)-t-butyloxycarbonylamino-3-(3-indolyl)propionamide and the resulting solution was stirred at 0° C. for 15 min. The ice bath was removed and the solution was allowed to warm to room temperature. After 30 min the reaction mixture was concentrated and the residue was partitioned between saturated NaHCO3 and CH2Cl2. The organic layer was washed with brine, dried and concentrated leaving 1.044 g of the title compound which was used in the next step without purification.

Workup

  1. customThe ice bath was removed
  2. temperatureto warm to room temperature
  3. concentrationAfter 30 min the reaction mixture was concentrated
  4. customthe residue was partitioned between saturated NaHCO3 and CH2Cl2
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c7c0e6045f034cd38c2a3de589d7939a
Source dataset
uspto-grants-1999_02
Patent number
US05869489

Reaction notes

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