Hydrochloric Acid → 1-(Piperazin-2-ylcarbonyl)-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide Trihydrochloride

HRID 2185437Notes

Reaction equation

HRID 2185437 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:32])[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][NH:15]2)[CH:3]=1.CO.[O:35]1[CH2:40][CH2:39]OCC1>>[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:32])[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:40]([CH:39]2[CH2:11][NH:2][CH2:3][CH2:4][NH:12]2)=[O:35])[CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 59895122trans-4-((R)-2-Hydroxy-4-Phenylbutrylamino)-L-Proline 3-Quinolylamide

Product 1

HCID 213414421-(Piperazin-2-ylcarbonyl)-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide Trihydrochloride

Procedure

A solution of 4 N hydrochloric acid in 1,4-dioxane (5 mL) was added to 1,4-di-(N-tert-butoxycarbonyl)piperazin-2-ylcarbonyl)-trans-4-((R)-2-hydroxy-4-phenylbutyrylamino)-L-proline 3-quinolylamide (C, 76 mg) at 0° C., and methanol (2 mL) was added to dissolve insoluble materials. After stirring for 1.5 hr, the reaction mixture was evaporated and coevaporated three times with 1,4-dioxane and ether in vacuo to give pale yellow solids. The solids were washed with ether to afford the title compound (64 mg) as a colorless solid: 1H NMR (400 MHz, D2O) δ 1.92-2.05 (m, 2H), 2.34-2.48 (m, 1H), 2.67(t, 2H), 3.24-4.89 (m, 13H), 7.15-7.32 (m, 5H), 7.83 (t, 1H), 7.96 (t, 1H), 8.09-8.16 (m, 2H), 8.94 (d, 1H), and 9.27 (d, 1H); mass spectrum (FAB+) m/e 531 (M+1); Anal. Calcd. for C29H34N6O4.3HCl.3H2O: C, 50.06; H, 6.26; N, 12.08. Found: C, 50.56; H, 6.34; N, 1.48.

Workup

  1. dissolutionto dissolve insoluble materials
  2. customthe reaction mixture was evaporated
  3. customto give pale yellow solids
  4. washThe solids were washed with ether

Sources & evidence

ORD record
ord-85f5cf4269b547159288548a48b40e2d
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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