Hydrochloric Acid → trans-4-Aminomethyl-L-Proline 4-Phenoxyphenylamide Dihydrochloride

HRID 2185464Notes

Reaction equation

HRID 2185464 reaction equation
[ClH:1].[O:2]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:38])[C@@H:17]2[CH2:21][C@@H:20]([CH2:22][NH:23]C(OC(C)(C)C)=O)[CH2:19][N:18]2C(OC(C)(C)C)=O)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[ClH:1].[ClH:1].[O:2]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:38])[C@@H:17]2[CH2:21][C@@H:20]([CH2:22][NH2:23])[CH2:19][NH:18]2)=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54074172trans-4-(N-tert-Butoxycarbonylaminomethyl)-N-tert-Butoxycarbonyl-L-Proline 4-Phenoxyphenylamide

Product 1

HCID 70177808trans-4-Aminomethyl-L-Proline 4-Phenoxyphenylamide Dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4 N hydrochloric acid in 1,4-dioxane (6 mL) was added to a solution of trans-4-(N-tert-butoxycarbonylaminomethyl)-N-tert-butoxycarbonyl-L-proline 4-phenoxyphenylamide (A, 182 mg) in 1,4-dioxane (6 mL) at room temperature. After stirring at room temperature for 20 min, the reaction mixture was concentrated in vacuo. The residue was washed with ether to give the title compound (95 mg) as a colorless solid: 1H NMR (400 MHz, D2O) δ 2.36 (m, 1 H), 2.60 (m, 1H), 2.82 (m, 1 H), 3.23 (m, 3 H), 3.85 (dd, J=7.5, 11.5 Hz, 1 H), 4.73 (dd, J=3.9, 9.3 Hz, 1 H), 7.08 (d, J=6.84 Hz, 2 H), 7.10 (d, J=6.84 Hz, 2 H), 7.22 (t, J=7.0 Hz, 1H), and 7.45 (m, 4 H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. washThe residue was washed with ether

Sources & evidence

ORD record
ord-e34185bc89254a8aad2590bb2fe839bf
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…