Hydrochloric Acid → HCID 21341579, compound

HRID 2185412Notes

Reaction equation

HRID 2185412 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:58])[C@@H:14]2[CH2:18][C@@H:17]([NH:19][C:20](=O)[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](=[O:57])[C@@H:33]2[CH2:37][C@@H:36]([NH:38]C(=O)CNC(OC(C)(C)C)=O)[CH2:35][N:34]2C(OC(C)(C)C)=O)[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:58])[C@@H:14]2[CH2:18][C@@H:17]([NH:19][CH2:20][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](=[O:57])[C@@H:33]2[CH2:37][C@@H:36]([NH2:38])[CH2:35][NH:34]2)[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21341561HCID 21341561, compound

Product 1

HCID 21341579HCID 21341579, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4 N hydrochloric acid in 1,4-dioxane (4 mL) was added to N-tert-butoxycarbonyl-trans-4-(N-tert-butoxycarbonylglycylamino)-L-prolyl-trans-4-((R)-2-hydroxy-4-phenylbutyrylamino)-L-proline 3-quinolylamide (P, 90 mg) at 0° C., and methanol was added until insoluble materials were disappeared. After stirring for 2 hr, the reaction mixture was evaporated and coevaporated several times with hexane and ethanol in vacuo to give pale yellow solids. The solids were washed with ether to afford the title compound (62 mg) as a colorless solid: 1H-NMR (400 MHz, D2O) δ 1.86-2.03(m, 2H), 2.28-2.47(m, 2H), 2.53-2.69(m, 4H), 3.42-3.50(m, 1H), 3.58-3.66(m, 1H), 3.86-3.94(m, 2H), 4.03-4.14(m, 2H), 4.38-4.46(m, 1H), 4.76-4.83(m, 1H), 4.87-4.94(m, 1H), 7.11-7.29(m, 5H), 7.78-7.84(m, 1H), 7.91-7.98(m,1H), 8.04-8.12(m, 2H), 8.91-8.94(m, 1H), and 9.03-9.28(m, 1H):; IR (KBr) 3300, 3023, 2937, 2852, 1701, 1657, 1651, 1610, 1574, 1549, 1495, 1485, and 1454 cm−1; mass spectrum (FAB+) m/e 531 (M+1); Anal. Calcd for C29H34 N6O4.3HCl.3H2O, C; 50.18, H; 6.24, N; 12.10. Found: C; 50.45, H; 6.15, N; 11.28.

Workup

  1. customthe reaction mixture was evaporated
  2. customto give pale yellow solids
  3. washThe solids were washed with ether

Sources & evidence

ORD record
ord-683466da54fe471fa208ffba0422f885
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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