Trifluoroacetic acid → 4-methyl-D-leucyl-N1-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-N2-cyclopropylglycinamide

HRID 857804Notes

Reaction equation

HRID 857804 reaction equation
C(O)(C(F)(F)F)=O.C(OC([NH:15][C@@H:16]([C:22]([N:24]([CH:42]1[CH2:44][CH2:43]1)[CH2:25][C:26]([NH:28][CH2:29][C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=1[N:37]1[CH:41]=[N:40][N:39]=[N:38]1)=[O:27])=[O:23])[CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=O)(C)(C)C>C(Cl)Cl>[CH3:19][C:18]([CH3:21])([CH3:20])[CH2:17][C@H:16]([C:22]([N:24]([CH:42]1[CH2:44][CH2:43]1)[CH2:25][C:26]([NH:28][CH2:29][C:30]1[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=1[N:37]1[CH:41]=[N:40][N:39]=[N:38]1)=[O:27])=[O:23])[NH2:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69656500N-(tert-butoxycarbonyl)-4-methyl-D-leucyl-N1-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-N2-cyclopropylglycinamide

Product 1

HCID 587601274-methyl-D-leucyl-N1-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-N2-cyclopropylglycinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (3 mL) was added to a solution of N-(tert-butoxycarbonyl)-4-methyl-D-leucyl-N1-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-N2-cyclopropylglycinamide (80 mg, 0.15 mmol) in CH2Cl2 (6 mL). The solution was stirred at room temperature for 30 min and the solvent was then removed in vacuo. The residue was taken up in DMF and purified by reverse phase HPLC. The product fractions were combined and reduced in vacuo and the residual oil was concentrated repeatedly from Et2O to give the title compound as a white foam. 1H NMR (500 MHz, CD3O): δ 9.52 (s, 1 H), 8.50 (m, 1 H), 7.68 (d, J=2.5 Hz, 1 H), 7.57 (dd, J=2.5, 8.5 Hz, 1 H), 7.50 (d, J=8.0 Hz, 1 H), 4.72 (dd, J=3.5, 8.5 Hz, 1 H), 4.28 (d, J=16.0 Hz, 1 H), 4.24 (d, J=15.5 Hz, 1 H), 4.10 (d, J=16.0 Hz, 1 H), 3.99 (d, J=16.0 Hz, 1 H), 2.91–2.86 (m, 1 H), 2.02 (dd, J=3.5, 15.5 Hz, 1 H), 1.70 (dd, J=8.5, 15.0 Hz, 1 H), 1.06 (s, 9 H), 1.03–0.86 (m, 4 H). HRMS (APCI, M+H): 434.2055 (found); 434.2066 (calculated).

Workup

  1. customthe solvent was then removed in vacuo
  2. custompurified by reverse phase HPLC
  3. concentrationthe residual oil was concentrated repeatedly from Et2O

Sources & evidence

ORD record
ord-1469b6a80bd04b29adeaadc9aaabd51c
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

Loading…