Trifluoroacetic acid → HCID 57265579, compound

HRID 1078156Notes

Reaction equation

HRID 1078156 reaction equation
C(OC([C@@:8]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([OH:29])[C@H:9]([NH:16][C@@H:17]1[CH2:23][C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[CH2:20][NH:19][C:18]1=[O:28])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:10]1([C@@H:9]([NH:16][C@@H:17]2[CH2:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[CH2:20][NH:19][C:18]2=[O:28])[C@H:8]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[OH:29])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67743936HCID 67743936, compound

Product 1

HCID 57265579HCID 57265579, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 478 mg (1.01 mmol) of 4(R)-[[t-butoxycarbonyl][(1R,2S)-1,2-diphenyl-2-hydroxyethyl]]amino-2,3,4,5-tetrahydro-1H-2-benzazepin-3-one (Example 1, Step B) in 5 mL of methylene chloride at room temperature was treated with 0.5 mL of trifluoroacetic acid. The mixture was stired at room temperature for 3 hours then all volatiles removed under vacuum. The residue was dissolved in 5 mL of water and the solution made basic (pH 10-11) by the addition of solid sodium carbonate. The mixture was extracted with chloroform (5×) and the combined extracts dried over anhydrous potassium carbonate, filtered and solvents removed under vacuum to give 372 mg (1.00 mmol, 99%) of 4(R)-[[(1R,2S)-1,2-diphenyl-2-hydroxyethyl]]amino-2,3,4,5-tetrahydro-1H-2-benzazepin-3-one which was used in the next step without purification.

Workup

  1. customall volatiles removed under vacuum
  2. dissolutionThe residue was dissolved in 5 mL of water
  3. additionby the addition of solid sodium carbonate
  4. extractionThe mixture was extracted with chloroform (5×)
  5. dry with materialthe combined extracts dried over anhydrous potassium carbonate
  6. filtrationfiltered
  7. customsolvents removed under vacuum

Sources & evidence

ORD record
ord-ffa960a393b44a7880afe1249b7d174f
Source dataset
uspto-grants-1996_08
Patent number
US05545735

Reaction notes

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