Hydrochloric Acid → trans-4-Glycylamino-L-Proline 4-Benzylphenylamide Dihydrochloride

HRID 2185452Notes

Reaction equation

HRID 2185452 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:40])[C@@H:16]2[CH2:20][C@@H:19]([NH:21][C:22](=[O:32])[CH2:23][NH:24]C(OC(C)(C)C)=O)[CH2:18][N:17]2C(OC(C)(C)C)=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:41]>O1CCOCC1>[ClH:41].[ClH:41].[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:40])[C@@H:16]2[CH2:20][C@@H:19]([NH:21][C:22](=[O:32])[CH2:23][NH2:24])[CH2:18][NH:17]2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131723253trans-4-(N-tert-Butoxycarbonylglycylamino)-N-tert-Butoxycarbonyl-L-Proline 4-Benzylphenylamide

Product 1

HCID 70176445trans-4-Glycylamino-L-Proline 4-Benzylphenylamide Dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

trans-4-(N-tert-Butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-L-proline 4-benzylphenylamide (A, 158 mg) was dissolved in 4 N hydrogen chloride in 1,4-dioxane (6 mL). After stirring for 2 hr, the reaction mixture was evaporated in vacuo to give white solids. The solids were washed with ether to afford the title compound (A, 103 mg): 1H NMR (400 MHz, D2O) δ 2.59 (dd, J=7.8, 6.4 Hz, 2H), 3.48 (dd, J=12.7, 4.8 Hz, 1H), 3.83 (dd, J=12.7, 6.4 Hz, 1H), 3.85 (s, 2H), 4.00 (s, 2H), 4.62 (m, 1H), 4.73 (m, 1H), and 7.28-7.42 (m, 9H).

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. customto give white solids
  3. washThe solids were washed with ether

Sources & evidence

ORD record
ord-785cd028a97c4637889a4a22bad0b86a
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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