Hydrochloric Acid → 1-(trans-4-Glycylamino-L-prolyl)-4-(3,5-dichlorophenoxy)piperidine Dihydrochloride

HRID 2185482Notes

Reaction equation

HRID 2185482 reaction equation
[ClH:1].C(OC([NH:9][CH2:10][C:11]([NH:13][C@H:14]1[CH2:18][N:17](C(OC(C)(C)C)=O)[C@H:16]([C:26]([N:28]2[CH2:33][CH2:32][CH:31]([O:34][C:35]3[CH:40]=[C:39]([Cl:41])[CH:38]=[C:37]([Cl:42])[CH:36]=3)[CH2:30][CH2:29]2)=[O:27])[CH2:15]1)=[O:12])=O)(C)(C)C>O1CCOCC1>[ClH:41].[ClH:1].[NH2:9][CH2:10][C:11]([NH:13][C@H:14]1[CH2:18][NH:17][C@H:16]([C:26]([N:28]2[CH2:33][CH2:32][CH:31]([O:34][C:35]3[CH:36]=[C:37]([Cl:42])[CH:38]=[C:39]([Cl:41])[CH:40]=3)[CH2:30][CH2:29]2)=[O:27])[CH2:15]1)=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 701730401-[trans-4-(n-Tert-butoxycarbonylglycylamino)-n-tert-butoxycarbonyl-l-prolyl]-4-(3,5-dichlorophenoxy)piperidine

Product 1

HCID 701757581-(trans-4-Glycylamino-L-prolyl)-4-(3,5-dichlorophenoxy)piperidine Dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4 N hydrochloric acid in 1,4-dioxane (13 mL) was added to a solution of 1-[trans-4-(N-tert-butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-L-prolyl]-4-(3,5-dichlorophenoxy)piperidine (C, 640 mg) in 1,4-dioxane (13 mL) at room temperature. After stirring at room temperature for 30 min, the reaction mixture was evaporated in vacuo. The residue was washed with ether to give the titled compound (361 mg) as white crystals: 1H NMR (400 MHz, D2O) δ 1.80 (br s, 2H), 2.03 (br s, 2H), 2.40 (m, 1H), 2.61 (m, 1H), 3.46-3.50 (m, 2H), 3.60 (br s, 1H), 3.77 (m, 3H), 3.86 (s, 2H), 4.58 (br s, 1H), 4.72 (br s, 1H), 5.03 (t, J=8.3 Hz, 1H), 7.03 (br s, 2H), and 7.10 (br s, 1H); mass spectrum (EI+) m/e 415.

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. washThe residue was washed with ether

Sources & evidence

ORD record
ord-53b79b06cd154c7d823bf7859295fbc3
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…