Trifluoroacetic acid → HCID 69749755, compound

HRID 2301049Notes

Reaction equation

HRID 2301049 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:14]=[C:13]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=1[NH:24][C:25](=[O:36])[C@H:26]([NH:28]C(OC(C)(C)C)=O)[CH3:27]>C(Cl)Cl>[Cl:8][C:9]1[CH:14]=[C:13]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:12]=[CH:11][C:10]=1[NH:24][C:25](=[O:36])[C@H:26]([NH2:28])[CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54454834HCID 54454834, compound

Product 1

HCID 69749755HCID 69749755, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 ml) was added drop wise to a solution of (R)-N-[2-chloro-4-(phenylsulphonyl)phenyl]-2-(t-butoxycarbonylamino)propanamide (Method 2) (0.090 g) in dry DCM (5 ml). The resulting mixture was stirred at room temperature for 3 hours. Volatile material was removed by evaporation. The resulting residue was re-dissolved in DCM (10 ml), and volatile material was removed by evaporation. This was repeated, the resulting residue was dried for 30 minutes on a high vacuum line. The residue was then dissolved in DCM and passed through a Varian Isolute SPE column containing basic residues, with DCM as the eluent to give the title compound (0.067 g) as a gum. NMR (CDCl3): 1.32-1.40 (d, 3H), 1.52 (brs, 2H), 3.51-3.64 (q, 1H), 7.40-7.55 (m, 3H), 7.71-7.8(m, 1H), 7.81-7.95 (m, 3H), 8.58-8.65 (m, 1H), 10.46 (brs, 1H). MS: (ESP−) 339.3 (M+H)+.

Workup

  1. customVolatile material was removed by evaporation
  2. dissolutionThe resulting residue was re-dissolved in DCM (10 ml)
  3. customvolatile material was removed by evaporation
  4. customthe resulting residue was dried for 30 minutes on a high vacuum line
  5. dissolutionThe residue was then dissolved in DCM
  6. additioncontaining basic residues

Sources & evidence

ORD record
ord-87cc20f6b02d4dab8ac93e3898485fe4
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

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