Hydrochloric Acid → trans-4-(N,N-Dimethylglycylamino)-L-Prolyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide Trihydrochloride

HRID 2185423Notes

Reaction equation

HRID 2185423 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:52])[C@@H:13]2[CH2:17][C@@H:16]([NH:18][C:19](=[O:30])[C@H:20]([OH:29])[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:15][N:14]2[C:31](=[O:51])[C@@H:32]2[CH2:36][C@@H:35]([NH:37][C:38](=[O:43])[CH2:39][N:40]([CH3:42])[CH3:41])[CH2:34][N:33]2C(OC(C)(C)C)=O)[CH:2]=1.[ClH:53]>O1CCOCC1>[ClH:53].[ClH:53].[ClH:53].[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:52])[C@@H:13]2[CH2:17][C@@H:16]([NH:18][C:19](=[O:30])[C@H:20]([OH:29])[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:15][N:14]2[C:31](=[O:51])[C@@H:32]2[CH2:36][C@@H:35]([NH:37][C:38](=[O:43])[CH2:39][N:40]([CH3:41])[CH3:42])[CH2:34][NH:33]2)[CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21341541N-tert-Butoxycarbonyl-trans-4-(N,N-Dimethylglycyl)amino-L-Prolyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide

Product 1

HCID 21341594trans-4-(N,N-Dimethylglycylamino)-L-Prolyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-Proline 3-Quinolylamide Trihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-tert-Butoxycarbonyl-trans-4-(N,N-dimethylglycylamino)-L-prolyl-trans-4-((R)-2-hydroxy-4-phenylbutyrylamino)-L-proline 3-quinolylamide (C, 76 mg) was dissolved in 4 N hydrogen chloride in 1,4-dioxane (10 mL) at 0° C., and stirred at 0†° C. for 5 min and at room temperature for 3 hr. The solution was evaporated in vacuo, and the residue was purified by HPLC (Shiseido, Capeell Pak C18 UG120, 3 cm×25 cm, 0.02 N hydrochloric acid:methanol=55:45, v/v) and freeze-dried from water to afford the title compound (28 mg) as a pale yellow powder: 1H NMR (400 MHz, D2O) δ 1.83-2.07 (m, 2H), 2.22-2.47 (m, 3H), 2.47-2.68 (m, 3H), 2.81 (s, 6H), 3.26-3.39 (m, 1H), 3.52-3.70 (m, 2H), 3.80-3.98 (m, 3H), 4.00-4.08 (m, 1), 4.31-4.52 (m, 2H), 4.68-4.84 (m, 2H), 7.07-7.29 (m, 5H), 7.73-7.81 (m, 1H),7.86-7.95 (m, 1H), 7.99-8.12 (m, 2H), 8.87 (s, 1H), and 9.21 (s, 1H); IR (KBr) 3367, 3025, 2952, 1654, 1648, 1610, 1571, 1554, and 1454 cm−1; mass spectrum (FAB+) m/e 616 (M+1); high-resolution mass (FAB) m/e Calcd for C33H41 N7O5: 616.3247. Found: 616.3237.

Workup

  1. waitat room temperature for 3 hr
  2. customThe solution was evaporated in vacuo
  3. customthe residue was purified by HPLC (Shiseido, Capeell Pak C18 UG120, 3 cm×25 cm, 0.02 N hydrochloric acid
  4. dry with materialmethanol=55:45, v/v) and freeze-dried from water

Sources & evidence

ORD record
ord-17a261d489b24f99a766c396d3088f24
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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