Hydrochloric Acid → HCID 21341591, compound

HRID 2185446Notes

Reaction equation

HRID 2185446 reaction equation
[ClH:1].[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:12][C:13](=[O:50])[C@@H:14]([CH2:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[NH:15][C:16](=[O:41])[C@@H:17]2[CH2:21][C@@H:20]([NH:22][C:23](=[O:33])[CH2:24][NH:25]C(OC(C)(C)C)=O)[CH2:19][N:18]2C(OC(C)(C)C)=O)[CH:3]=1>O1CCOCC1.CO>[ClH:1].[ClH:1].[ClH:1].[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:12][C:13](=[O:50])[C@@H:14]([CH2:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[NH:15][C:16](=[O:41])[C@@H:17]2[CH2:21][C@@H:20]([NH:22][C:23](=[O:33])[CH2:24][NH2:25])[CH2:19][NH:18]2)[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21341605HCID 21341605, compound

Product 1

HCID 21341591HCID 21341591, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4 N hydrogen chloride in 1,4-dioxane (10 mL) was added to a solution of trans-4-(N-tert-butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-L-prolyl-D-homophenylalanine 3-quinolylamide (C, 162 mg) in methanol (10 mL) at 0° C. After stirring at 0° C. for 5 min and at room temperature for 3 hr, the solution was concentrated in vacuo. The residue was purified by HPLC(Shiseido, Capcell Pak C18 UG120, 3 cm×25 cm, 0.02 N hydrochloric acid: methanol=65:35, v/v) and freeze-dried from water to afford the title compound (90 mg) as a pale yellow powder: 1H NMR (400 MHz, D2O) δ 2.18-2.43 (m, 3H), 2.43-2.57 (m, 1H), 2.74-2.96 (m, 2H), 3.40 (dd, J=12.2,4.4 Hz, 1H), 3.76-3.87 (m, 3H), 4.45-4.60 (m, 2H), 4.61-4.73 (m, 1H), 7.01-7.17 (m, 1H), 7.17-7.31 (m, 4H), 7.86 (t, J=7.8 Hz, 1H), 8.00 (t, J=7.8 Hz, 1H), 8.04-8.19 (m, 2H), 8.81 (s, 1H), and 9.15 (s, 1H); IR (KBr) 3388, 3205, 3037, 1685, 1681, 1610, 1571, 1552, 1496, 1486, and 1454 cm−1; mass spectrum (EI+) m/e 474 (M+); (FAB+) m/e 475 (M+1); Anal. Calcd for 26H30N6O3.3HCl.3H2O: C, 48.95; H, 6.16; N, 13.17. Found: C, 49.16; H, 5.90; N, 13.15.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customThe residue was purified by HPLC(Shiseido, Capcell Pak C18 UG120, 3 cm×25 cm, 0.02 N hydrochloric acid
  3. dry with materialmethanol=65:35, v/v) and freeze-dried from water

Sources & evidence

ORD record
ord-6c02c647d38c4ae9a8da880217d26c60
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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