Trifluoroacetic acid → HCID 86749246, compound

HRID 2396088Notes

Reaction equation

HRID 2396088 reaction equation
C(OC([NH:8][C@@H:9]([CH2:19][S:20]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:10][N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=O)(C)(C)C.[Cl:40][C:41]1[C:49]([Cl:50])=[CH:48][CH:47]=[CH:46][C:42]=1[C:43]([NH2:45])=[O:44].C(C(O)=O)(F)(F)F.C([SiH](CC)CC)C>C(Cl)Cl>[NH2:8][C@@H:9]([CH2:19][SH:20])[CH2:10][N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14].[Cl:40][C:41]1[C:49]([Cl:50])=[CH:48][CH:47]=[CH:46][C:42]=1[C:43]([NH2:45])=[O:44]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67768232HCID 67768232, compound

Product 1

HCID 86749246HCID 86749246, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[2(R)-t-Butoxycarbonylamino-3-triphenylmethylmercaptopropyl]-L-proline-2,3-dichlorobenzamide (0.097 g, 0.14 mmol) was dissolved in CH2Cl2(3 mL), CF3CO2H (1 mL) at ambient temperature, treated with triethylsilane (0.088 mL, 0.55 mmol) and stirred for 1 h. The reaction mixture was triturated with 0.1% TFA in H2O, filtered, concentrated and chromatographed by RP-HPLC and lyophilized. The residue was dissolved in MeOH (1 mL), treated with concd HCl, concentrated and triturated with Et2O to provide the title compound as the his hydrochloride salt. 1H NMR (CD3OD) δ 7.50 (d, 1H, J=6 Hz), 7.27-7.4 (m, 2H),4.60 (ABq, 2H), 4.25-4.7 (m, 1H), 3.3-3.9 (m, 5H), 2.99 (d, 2H, J=5 Hz), 2.5-2.7 (m, 1H), 2.0-2.3 (m, 3H).

Workup

  1. customThe reaction mixture was triturated with 0.1% TFA in H2O
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customchromatographed by RP-HPLC
  5. dissolutionThe residue was dissolved in MeOH (1 mL)
  6. additiontreated with concd HCl
  7. concentrationconcentrated
  8. customtriturated with Et2O

Sources & evidence

ORD record
ord-b336e46afc034c61a3b725889434c987
Source dataset
uspto-grants-1996_02
Patent number
US05491164

Reaction notes

Loading…