Hydrochloric Acid → HCID 21341587, compound

HRID 2185450Notes

Reaction equation

HRID 2185450 reaction equation
[ClH:1].[Cl:2][C:3]1[CH:42]=[CH:41][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:40])[C@@H:16]3[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]3C(OC(C)(C)C)=O)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1>O1CCOCC1>[ClH:2].[ClH:1].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:40])[C@@H:16]3[CH2:20][C@@H:19]([NH:21][C:22](=[O:32])[CH2:23][NH2:24])[CH2:18][NH:17]3)=[CH:10][CH:9]=2)=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131723252HCID 131723252, compound

Product 1

HCID 21341587HCID 21341587, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4 N hydrochloric acid in 1,4-dioxane (5 mL) was added to a solution of trans-4-(N-tert-butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-L-proline 4-(4′-chlorophenoxy)phenylamide (A, 230 mg) in 1,4-dioxane (5 mL) at room temperature. After stirring at room temperature for 1 hr, the reaction mixture was concentrated in vacuo. The residue was washed with ether to give the title compound (112 mg) as colorless crystals: 1H NMR (400 MHz, D2O) δ 2.31 (quintet, J=7.0 Hz, 1 H), 2.59 (m, 1 H), 3.53 (m, 1 H), 3.74 (m, 1 H), 3.88 (s, 2 H), 4.50 br s, 1 H), 4.80 (m, 1 H), 6.65 (d, J=7.8 Hz, 2 H), 6.72 (d, J=7.8 Hz, 2 H), 7.03 (d, J=7.8 Hz, 2 H), and 7.39 (d, J=7.8 Hz, 2 H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. washThe residue was washed with ether

Sources & evidence

ORD record
ord-3b21ad5016cd45eca7d1436746bfd940
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…