Hydrochloric Acid → HCID 70176970, compound

HRID 2185449Notes

Reaction equation

HRID 2185449 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:35]=[CH:34][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:33])[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][NH:17]3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1>O1CCOCC1>[ClH:1].[ClH:1].[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:33])[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:12][CH:13]=2)=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21341608HCID 21341608, compound

Product 1

HCID 70176970HCID 70176970, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4 N hydrochloric acid in 1,4-dioxane (6 mL) was added to a solution of trans-4-(N-tert-butoxylcarbonylglycylamino)-L-Proline 4-(4′-methylphenoxy)phenylamide (A, 210 mg) in 1,4-dioxane (6 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 (106 mg) as colorless crystals: 1H NMR (400 MHz, D2O) δ 1.28 (s, 3 H), 2.59 (m, 2 H), 3.50 (br d, J=8.8 Hz, 1H), 3.82 (t, J=6.0 Hz, 1H), 3.87 (s, 2 H), 4.61 (br s, 1 H), 4.96 (m, 1 H), 6.92 (d, J=7.5 Hz, 2 H), 7.00 (d, J=7.8 Hz, 2 H), 7.19 (d, J=7.5 Hz, 2 H), and 7.43 (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-48c9870dad0546bbb1dc2a5a5b99e17a
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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