Trifluoroacetic acid → HCID 67023668, compound

HRID 491889Notes

Reaction equation

HRID 491889 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH2:9][CH2:10][C:11](=[O:25])[N:12]([CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:13][C:14]1[NH:15][CH:16]=[CH:17][N:18]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C@H:8]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH2:9][CH2:10][C:11]([N:12]([CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)[CH2:13][C:14]1[NH:18][CH:17]=[CH:16][N:15]=1)=[O:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67023582HCID 67023582, compound

Product 1

HCID 67023668HCID 67023668, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the white solid (2.60 g, 5.8 mmole) isolated in Step B above, in dichloromethane (45 mL) was added trifluoroacetic acid (45 mL). The resulting solution was stirred at room temperature for 2 hours. The solution was then concentrated. Hydrochloric acid solution (1N, 10 mL) was added and the resulting solution washed with diethyl ether one time. Sodium bicarbonate was added until there was no bubbling observed from the aqueous solution. The solution was extracted with ethyl acetate three times. The combined ethyl acetate extracts were dried over magnesium sulfate. The resulting solution was filtered and concentrated to yield 4-amino-4-(S),N-dicyclohexyl-N-(1H-imidazol-2-ylmethyl)-butyramide as a white solid.

Workup

  1. concentrationThe solution was then concentrated
  2. additionHydrochloric acid solution (1N, 10 mL) was added
  3. washthe resulting solution washed with diethyl ether one time
  4. additionSodium bicarbonate was added until there
  5. extractionThe solution was extracted with ethyl acetate three times
  6. dry with materialThe combined ethyl acetate extracts were dried over magnesium sulfate
  7. filtrationThe resulting solution was filtered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-22462304878e482a9485a56dd68b9f28
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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