(2s,4r)-4-(n-Tert-butoxycarbonylglycylamino)-2-(4-biphenyloxy)methyl-n-tert-butoxycarbonylpyrrolidine → (2S,4R)-4-Glycylamino-2-(4-Biphenyloxy)methylpyrrolidine

HRID 2185490Notes

Reaction equation

HRID 2185490 reaction equation
C(OC([NH:8][CH2:9][C:10]([NH:12][C@H:13]1[CH2:17][N:16](C(OC(C)(C)C)=O)[C@H:15]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)[CH2:14]1)=[O:11])=O)(C)(C)C>Cl.O1CCOCC1>[NH2:8][CH2:9][C:10]([NH:12][C@H:13]1[CH2:17][NH:16][C@H:15]([CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)[CH2:14]1)=[O:11]

Participants

4

Reactant 1

HCID 70177840(2s,4r)-4-(n-Tert-butoxycarbonylglycylamino)-2-(4-biphenyloxy)methyl-n-tert-butoxycarbonylpyrrolidine

Product 1

HCID 70177991(2S,4R)-4-Glycylamino-2-(4-Biphenyloxy)methylpyrrolidineYield 95.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(2S,4R)-4-(N-tert-Butoxycarbonylglycylamino)-2-(4-biphenyloxy)methyl-N-tert-butoxycarbonylpyrrolidine (B, 431 mg) was dissolved in 4 N hydrogen chloride in 1,4-dioxane (4 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 (254 mg): 1H NMR (400 MHz, D2O) δ 2.33 (m, 1H), 2.44 (m, 1H), 3.45 (dd, J=12.7, 4.4 Hz, 1H), 3.79 (dd, J=12.7, 6.8 Hz, 1H), 3.84 (s, 2H), 4.27 (dd, J=10.7, 6.8 Hz, 1H), 4.36 (m, 1H), 4.47 (d, J=10.7 Hz, 1H), 4.67 (m, 1H), 7.16 (d, J=8.3 Hz, 2H), 7.43 (d, J=7.3 Hz, 1H), 7.53 (t, J=7.3 Hz, 2H), 7.68-7.72 (m, 4H).

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-369c1aded8e44aa384cc03229d8b7e05
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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