Hydrochloric Acid → 1-(trans-4-Glycylamino-L-Prolyl)-4-(2-Chloro-5-Methylphenoxy)piperidine Dihydrochloride

HRID 2185487Notes

Reaction equation

HRID 2185487 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]([CH3:41])[CH:38]=[CH:37][C:36]=3[Cl:42])[CH2:30][CH2:29]2)=[O:27])[CH2:15]1)=[O:12])=O)(C)(C)C>O1CCOCC1>[ClH:42].[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:40]=[C:39]([CH3:41])[CH:38]=[CH:37][C:36]=3[Cl:42])[CH2:30][CH2:29]2)=[O:27])[CH2:15]1)=[O:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 701767841-[trans-4-(n-Tert-butoxycarbonylglycylamino)-n-tert-butoxycarbonyl-l-prolyl]-4-(2-chloro-5-methylphenoxy)piperidine

Product 1

HCID 701771821-(trans-4-Glycylamino-L-Prolyl)-4-(2-Chloro-5-Methylphenoxy)piperidine Dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4 N hydrochloric acid in 1,4-dioxane (8 mL) was added to a solution of 1-[trans-4-(N-tert-butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-L-prolyl]-4-(2-chloro-5-methylphenoxy)piperidine (C, 280 mg) in 1,4-dioxane (8 mL) at room temperature. After stirring at room temperature for 20 min, the reaction mixture was evaporated in vacuo. The residue was washed with ether to give the titled compound (142 mg) as a white powder: 1H NMR (400 MHz, D2O) δ 1.90-2.01 (4H), 2.32 (s, 3H), 2.43 (m, 1H), 2.61 (br s, 1H), 3.49 (br t, 2H), 3.67 (br s, 1H), 3.79 (m, 4H), 3.85 (s, 2H), 4.58 (br s, 1H), 5.02 (m, 1H), 6.91 (d, J=8.0 Hz, 1H), 7.09 (s, 1H), and 7.35 (d, J=8.0 Hz, 1H); mass spectrum (EI+) m/e 394 (M).

Workup

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

Sources & evidence

ORD record
ord-6a6ae7232a1e4d7bbe5234bc4abf8c76
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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