Hydrochloric Acid → HCID 21341465, compound

HRID 2185440Notes

Reaction equation

HRID 2185440 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]2[CH2:18][C@@H:17]([NH:19][C:20](=[O:31])[C@H:21]([OH:30])[CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:16][N:15]2[C:32]([CH:34]2[CH2:39][N:38]([C:40](=[NH:42])[CH3:41])[CH2:37][CH2:36][N:35]2C(OC(C)(C)C)=O)=[O:33])[CH:3]=1.CO>O1CCOCC1>[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]2[CH2:18][C@@H:17]([NH:19][C:20](=[O:31])[C@H:21]([OH:30])[CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:16][N:15]2[C:32]([CH:34]2[CH2:39][N:38]([C:40](=[NH:42])[CH3:41])[CH2:37][CH2:36][NH:35]2)=[O:33])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21341444HCID 21341444, compound

Product 1

HCID 21341465HCID 21341465, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

4 N Hydrochloric acid in 1,4-dioxane (10 mL) was added to crude (1-tert-butoxycarbonyl-4-acetimidoylpiperazin-2-ylcarbonyl)-trans-4-((R)-2-hydroxy-4-phenylbutyrylamino)-L-proline 3-quinolylamide (D) at 0° C. After stirring at 0° C. for 10 min and at room temperature for 10 min, methanol (2 mL) was added until insoluble materials were disappeared. After stirring for 1 hr, the solvents were removed in vacuo. The residue was purified by HPLC (Shiseido, Capcell Pak C18 UG120, 3 cm×25 cm, 0.02 N hydrochloric acid:methanol=70:30 to 60:40, v/v) and freeze-dried from water to afford the title compound (37 mg) as a pale yellow powder. The compound appears as a mixture of rotamers: 1H NMR (400 MHz, D2O) δ 1.78-2.00 (2H, m), 2.26 and 2.32 (each s, total 3H), 2.20-2.43 (m, 1H), 2.52-2.66 (m, 2H), 3.18-3.72 (m, 6H), 3.87-4.13 (m, 3H), 4.30-4.44 (m, 2H), 4.52-4.66 (m, 1H), 4.73-4.82 (m, 1H), 7.04-7.27 (m, 5H), 7.77 (t, J=7.8 Hz, 1H), 7.92 (t, J=7.8 Hz, 1H), 8.00-8.12 (m, 2H), 8.91 (s, 1H), and 9.25 (s, 1H); IR (KBr) 3064, 1658, 1612, 1571, 1550, 1494, and 1454 cm−1; mass spectrum (FAB+) m/e 572 (M+1); Anal.Calcd for C31H37N7O4.3HCl.6.1H2O: C, 47.07; H, 6.65; N, 12.40. Found: C, 46.68; H, 6.11; N, 12.02.

Workup

  1. stirringAfter stirring for 1 hr
  2. customthe solvents were removed in vacuo
  3. customThe residue was purified by HPLC (Shiseido, Capcell Pak C18 UG120, 3 cm×25 cm, 0.02 N hydrochloric acid
  4. dry with materialmethanol=70:30 to 60:40, v/v) and freeze-dried from water

Sources & evidence

ORD record
ord-2b64339cee934d469fc630aee38e1838
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…