Diethyl Ether → HCID 86643596, compound

HRID 2381026Notes

Reaction equation

HRID 2381026 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:30](=[O:33])[NH:31][CH3:32])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16]CC2C=CC=CC=2)=[C:12]([O:24][C:25](=[O:29])[NH:26][CH2:27][CH3:28])[CH:11]=1)(C)(C)C.CCOCC.[ClH:40].O1CCOCC1>CO.[Pd]>[Cl-:40].[CH2:27]([NH:26][C:25]([O:24][C:12]1[CH:11]=[C:10]([CH2:9][C@H:8]([NH3+:7])[C:30](=[O:33])[NH:31][CH3:32])[CH:15]=[CH:14][C:13]=1[OH:16])=[O:29])[CH3:28]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 204431481,4-Dioxane hydrochlorideHCID 68726942HCID 68726942, compound

Product 1

HCID 86643596HCID 86643596, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

[(S)-2-(4-Benzyloxy-3-ethylcarbamoyloxy-phenyl)-1-methylcarbamoyl-ethyl]-carbamic acid tert-butyl ester (243 mg) was suspended in 4M HCl-dioxane (5 ml) and stirred at room temperature for 1 hour. The clear solution was evaporated to dryness giving an oil which was redissolved in methanol (5 ml). 5% Pd—C (50 mg) was added and the mixture stirred under an atmosphere of hydrogen gas at room temperature for 2 hours. The catalyst was removed by filtration and washed with methanol. Evaporation of the filtrate gave the crude product as an oil. Trituration with ether gave (S)-2-(3-ethylcarbamoyloxy-4-hydroxy-phenyl)-1-methylcarbamoyl-ethyl-ammonium chloride as a grey solid, 150 mg; NMR (500 MHz, d6 DMSO) 1.07 (3H, t J 7), 2.59 (3H, d J 4.5 collapse to s with D2O), 2.82-2.95 (2H, m), 3.03-3.10 (2H, m), 3.83 (1H, t J 7), 6.81-6.85 (3H, m), 7.55 (1H, t J 5.5), 8.19 (3H, br exch D2O), 8.37 (1H, br q exch D2O), 9.5 (1H, s, exch D2O); HPLC/MS Retention time 2.9 min, m/z 282 (MH+).

Workup

  1. customThe clear solution was evaporated to dryness
  2. customgiving an oil which
  3. stirringthe mixture stirred under an atmosphere of hydrogen gas at room temperature for 2 hours
  4. customThe catalyst was removed by filtration
  5. washwashed with methanol
  6. customEvaporation of the filtrate
  7. customgave the crude product as an oil

Sources & evidence

ORD record
ord-c8c70022ee1d40b997d11ea18b6d42a2
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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