Water → H-Gly-Gly-Gly-beta-Ala-OtBu

HRID 1914451Notes

Reaction equation

HRID 1914451 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([NH:13][CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12])=[O:8])=[O:4].O>CO.[Pd]>[NH2:1][CH2:2][C:3]([NH:5][CH2:6][C:7]([NH:9][CH2:10][C:11]([NH:13][CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12])=[O:8])=[O:4]

Participants

5

Reactant 2

HCID 962WaterHCID 57945504Z-Gly-Gly-Gly-beta-Ala-OtBu

Product 1

HCID 57945502H-Gly-Gly-Gly-beta-Ala-OtBuYield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.3 g (2.89 mmol) of Z-Gly-Gly-Gly-β-Ala-OtBu was dissolved in 80 mL of 95:5 methanol:deionized water in a 250 mL parr shaker flask to which was added 0.12 g of 10% palladium on carbon. The flask was shaken under a hydrogen atmosphere (42 PSI) for 7 hours. The mixture was vacuum filtered through celite filter aid and the filtrate was concentrated by rotary evaporation under vacuum to give 0.88 g (96%) of the title compound. 1H NMR (d6-DMSO) 8.12 (t, J=1.6 Hz 2H), 8.08 (t, J=1.6 Hz, 1H), 3.75 (s, 2H), 3.64 (d, J=5.9 2H), 3.28 (bs, 2H), 3.24 (q, J=6.0 Hz, 2H), 3.13 (s, 2H), 2.35 (t, J=6.8 Hz, 2H), 1.39 (s, 9H). 13C NMR (d6-DMSO) 173.38, 170.46, 169.18, 168.70, 79.89, 44.65, 41.95, 34.88, 34.78, 27.71. HRMS (M+H+) Calc. 317.1825. found 317.1801

Workup

  1. filtrationfiltered through celite
  2. filtrationfilter aid
  3. concentrationthe filtrate was concentrated by rotary evaporation under vacuum

Sources & evidence

ORD record
ord-75729a9121bd4f4f9b9e67d87bf167b2
Source dataset
uspto-grants-2013_12
Patent number
US08613930B2

Reaction notes

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