N-tert-Butoxycarbonyl-trans-4-(N-tert-Butoxycarbonylglycylamino)-D-Prolyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-proline 3-Quinolylamide → trans-4-Glycylamino-D-Prolyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-proline 3-Quinolylamide

HRID 2185419Notes

Reaction equation

HRID 2185419 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:57])[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:56])[C@H:32]2[CH2:36][C@H:35]([NH:37][C:38](=[O:48])[CH2:39][NH:40]C(OC(C)(C)C)=O)[CH2:34][N:33]2C(OC(C)(C)C)=O)[CH:2]=1>CO>[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:57])[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:56])[C@H:32]2[CH2:36][C@H:35]([NH:37][C:38](=[O:48])[CH2:39][NH2:40])[CH2:34][NH:33]2)[CH:2]=1

Participants

3

Reactant 1

HCID 21341554N-tert-Butoxycarbonyl-trans-4-(N-tert-Butoxycarbonylglycylamino)-D-Prolyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-proline 3-Quinolylamide

Product 1

HCID 21341428trans-4-Glycylamino-D-Prolyl-trans-4-((R)-2-Hydroxy-4-Phenylbutyrylamino)-L-proline 3-QuinolylamideYield 108.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-tert-butoxycarbonyl-trans-4-(N-tert-butoxycarbonylglycylamino)-D-prolyl-trans-4-((R)-2-hydroxy-4-phenylbutyrylamino)-L-proline 3-quinolylamide (G, 120 mg) at 0° C., and methanol (3 mL) was added to dissolve until insoluble materials. After stirring for 2 hr, the reaction mixture was evaporated and coevaporated with 1,4-dioxane and ether in vacuo to give solid. The solids were washed with ether to afford the title compound (97 mg) as a colorless solid: 1H NMR (400 MHz, D2O) δ 1.86-2.03 (m, 2H), 2.24-2.45 (m, 3H), 2.59-2.63 (m, 2H), 3.32 (m, 1H), 3.40-3.45 (m, 1H), 3.60-3.70 (m, 3H), 3.92-4.07 (m, 2H), 4.35-4.42 (m, 2H), 4.61-4.79 (m, 4H), 7.06-7.24 (m, 5H), 7.76 (t, 1H), 7.90 (t, 1H), 8.03 (d, 1H), 8.05(d, 1H), 8.86(s,1H), and 9.21 (s, 1H); mass spectrum (FAB+) m/e 588 (M+1); Anal. Calcd. For C31H37N7O5.3HCl.2H2O: C, 50.79; H, 6.05; N, 13.37. Found: C, 51.09; H, 6.07; N, 12.97.

Workup

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

Sources & evidence

ORD record
ord-30b773e0c05743ecb90e8eb2a454e88b
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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