Hydrochloric Acid → HCID 70048523, compound

HRID 1768912Notes

Reaction equation

HRID 1768912 reaction equation
[C:1]([O:5][C:6](=[O:33])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:32])[C@H:13]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[NH:14]C(OCC1C=CC=CC=1)=O)([CH3:4])([CH3:3])[CH3:2].[ClH:34]>O1CCCC1.[Pd]>[ClH:34].[C:1]([O:5][C:6](=[O:33])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:32])[C@@H:13]([CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[NH2:14])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 13021285HCID 13021285, compound

Product 1

HCID 70048523HCID 70048523, compoundYield 106.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a well-stirred, nitrogen-blanketed mixture of benzyloxycarbonyl-L-phenylalanyl-L-proline tert-butyl ester (23.00 g, 50.82 mmol) and 1[hydrochloric acid (51 mL, 51 mmol) in tetrahydrofuran (500 mL) was added 10% palladium on carbon (2.3 g). The suspension was stirred at ambient temperature for about 5 minutes before the nitrogen blanket was removed and replaced with hydrogen at one atmosphere. After about 5 hours, the suspension was suction-filtered through Celite and the filtrate was concentrated down to dryness to afford 19.17 g (100%) of the title compound as a dense, white solid, m.p. 168°-170° C.; 1H NMR (D2O) δ 7.41-7.38 (m, 3H), 7.28-7.26 (m, 2H), 4.56-4.51 (m, 1H), 4.20-4.16 (m, 1H), 3.53-3.46 (m, 1H), 3.27-3.21 (m, 1H), 3.14-3.07 (m, 1H), 2.72-2.64 (m, 1H), 2.05-1.65 (m, 4H), 1.58-1.49 (m, 1H), 1.45 (s, 9H); 13C NMR (D2O) ppm 174.85, 169.57, 135.40, 131.49, 131.10, 130.16, 86.09, 62.33, 54.82, 51.95, 49.51, 38.59, 30.63, 29.11, 25.88; IR (KBr, cm-1) 3242, 2980 , 2930, 2874, 1750, 1730, 1658, 1524, 1488, 1452, 1366, 1150; MS m/z (MH+ -HCl) calcd 319.2022, obsd 319.2013.

Workup

  1. customwas removed
  2. waitAfter about 5 hours
  3. filtrationthe suspension was suction-filtered through Celite
  4. concentrationthe filtrate was concentrated down to dryness

Sources & evidence

ORD record
ord-add912ca4a4a48598e4d80657de71806
Source dataset
uspto-grants-1995_01
Patent number
US05380713

Reaction notes

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