Hydrochloric Acid → HCID 178478813, compound

HRID 1768910Notes

Reaction equation

HRID 1768910 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9]([N:11]2[CH2:38][CH2:37][CH2:36][C@H:12]2[C:13]([NH:15][C@H:16]([CH:34]=[O:35])[CH2:17][CH2:18][CH2:19][N:20](C(OCC2C=CC=CC=2)=O)[C:21](=[NH:23])[NH2:22])=[O:14])=[O:10])[CH:2]=1.[ClH:39]>[Pd].O1CCCC1>[ClH:39].[ClH:39].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][C:9]([N:11]2[CH2:38][CH2:37][CH2:36][C@H:12]2[C:13]([NH:15][C@H:16]([CH:34]=[O:35])[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[NH:22])[NH2:23])=[O:14])=[O:10])[CH:2]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54295477HCID 54295477, compound

Product 1

HCID 178478813HCID 178478813, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on carbon (10%, 93 mg) was added to a well-stirred, nitrogen-blanketed mixture of N60 [N-(3-(3-pyridyl)propanoyl)-L-prolyl]-Nδ -benzyloxycarbonyl-L-arginine aldehyde (935.0 mg, 1.79 mmol) and 1N hydrochloric acid (0.90 mL) in tetrahydrofuran (20 mL). The mixture was stirred at room temperature for about 5 minutes before the nitrogen blanket was removed and replaced with hydrogen at one atmosphere. After about 5 hours, an additional equivalent of 1N hydrochloric acid (0.90 mL) was added and the mixture was suction-filtered through Celite and concentrated down to dryness to give 800.1 mg (97%) of the title compound as a dense, white solid, m.p. 126°-144° C. (sealed tube, decomposes between 190°-210° C.); 1H NMR (D2O) δ 8.69 (s, 1H), 8.65 (d, J=5.9 Hz, 1H), 8.53 (d, J=7.7 Hz, 1H), 8.01 (t, J=6.1 Hz, 1H), 4.38-4.34 (m, 1H), 4.11-3.81 (series of m, 1H), 3.63-3.51 (m, 3H), 3.18-3.14 (m, 2H), 2.95-2.80 (m, 2H), 2.27-2.21 (m, 2H), 2.00-1.50 (series of m, 5H); 13C NMR (D2O) ppm 176.75, 176.00, 175.23, 174.64, 156.55, 149.10, 143.54, 142.65, 140.87, 129.02, 124.66, 118.79, 95.08, 92.48, 79.24, 78.46, 62.78, 62.54, 62.30, 55.89, 51.43, 50.00, 49.34, 45.53, 42.79, 41.94, 35.72, 31.91, 31.81, 28.92, 27.56, 26.38, 25.98, 24.82, 24.62, 22.56; IR (KBr, cm-1) 3344-2876, 1654, 1554, 1448, 1248, 1000, 682. MS m/z (MH+ -2HCL) calcd 89.2301, obsd 389.2305.

Workup

  1. customwas removed
  2. waitAfter about 5 hours
  3. additionan additional equivalent of 1N hydrochloric acid (0.90 mL) was added
  4. filtrationthe mixture was suction-filtered through Celite
  5. concentrationconcentrated down to dryness

Sources & evidence

ORD record
ord-17d37ca4141b4ffb82cde16a61a61f10
Source dataset
uspto-grants-1995_01
Patent number
US05380713

Reaction notes

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