trans-4-(3-Biphenyloxy) N-tert-butoxycarbonyl-L-proline 2-(N-tert-butoxycarbonylamino)ethylamide → HCID 21341421, compound

HRID 2185492Notes

Reaction equation

HRID 2185492 reaction equation
C(OC([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:38])[C@@H:13]1[CH2:17][C@@H:16]([O:18][C:19]2[CH:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:22]=[CH:23][CH:24]=2)[CH2:15][N:14]1C(OC(C)(C)C)=O)=O)(C)(C)C>Cl.O1CCOCC1>[NH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:38])[C@@H:13]1[CH2:17][C@@H:16]([O:18][C:19]2[CH:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:22]=[CH:23][CH:24]=2)[CH2:15][NH:14]1

Participants

4

Reactant 1

HCID 54515339trans-4-(3-Biphenyloxy) N-tert-butoxycarbonyl-L-proline 2-(N-tert-butoxycarbonylamino)ethylamide

Product 1

HCID 21341421HCID 21341421, compoundYield 108.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

trans-4-(3-Biphenyloxy) N-tert-butoxycarbonyl-L-proline 2-(N-tert-butoxycarbonylamino)ethylamide (C, 175 mg) was dissolved in 4 N hydrogen chloride in 1,4-dioxane (3 mL). After stirring for 2 hr, the reaction mixture was evaporated in vacuo to give a white solid. The solid was washed with ether to afford the titled compound (118 mg): 1H NMR (400 MHz, D2O) δ 2.43 (m, 1H), 2.83 (m, 1H), 3.22 (m, 2H), 3.57 (m, 1H), 3.66 (m, 1H), 4.69-4.84 (m, 3H), 5.44 (m, 1H), 7.08 (d, J=8.3 Hz, 1H), 7.32 (s, 1H), 7.43 (d, J=7.8 Hz, 1H), 7.46-7.58 (m, 4H), and 7.73 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-70606ee8e8dc4760a25f901cc055fb2f
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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