Diethyl Ether → HCID 86643597, compound

HRID 2381029Notes

Reaction equation

HRID 2381029 reaction equation
[CH3:1][O:2][C:3](=[O:40])[C:4]([NH:7][C:8](=[O:39])[C@@H:9]([NH:31]C(OC(C)(C)C)=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[C:13]([O:25][C:26](=[O:30])[NH:27][CH2:28][CH3:29])[CH:12]=1)([CH3:6])[CH3:5].CCOCC.[ClH:46].O1CCOCC1>>[Cl-:46].[CH2:28]([NH:27][C:26]([O:25][C:13]1[CH:12]=[C:11]([CH2:10][C@H:9]([NH3+:31])[C:8](=[O:39])[NH:7][C:4]([C:3]([O:2][CH3:1])=[O:40])([CH3:6])[CH3:5])[CH:16]=[CH:15][C:14]=1[OH:17])=[O:30])[CH3:29]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 204431481,4-Dioxane hydrochlorideHCID 68725794HCID 68725794, compound

Product 1

HCID 86643597HCID 86643597, compound

Procedure

2-[(S)-3-(4-Benzyloxy-3-ethylcarbamoyloxy-phenyl)-2-tert-butoxycarbony lamino-propionylamino]-2-methyl-propionic acid methyl ester (380 mg) was dissolved in 4M HCl-dioxane (10 ml) and stirred at room temperature for 1 hour. The solution was evaporated to dryness and the resulting gum was redissolved on methanol (10 ml) containing 5% Pd—C (60 mg). The mixture was stirred under an atmosphere of hydrogen for 2 hours. The catalyst was removed by filtration and the filtrate evaporated to dryness giving a gum. Repeated trituration with ether gave (S)-2-(3-ethylcarbamoyloxy-4-hydroxy-phenyl)-1-(1-methoxycarbonyl-1-methyl-ethylcarbamoyl)-ethyl-ammonium chloride as a white solid, 240 mg; NMR (500 MHz, d6 DMSO) 1.07 (ca 3H, t J 7), 1.32 (3H, s), 1.38 (3H, s), 2.85 (1H, dd J 14, 7), 2.98 (1H, dd J 14, 5), 3.05-3.09 (2H, m), 3.58 (3H, s), 3.91 (1H, br t), 6.83 (1H, d J 8), 6.91 (1H, dd J 8, 2), 6.94 (1H, d J 2), 7.55 (1H, br t), 8.15 (3H, br s exch D2O), 8.82 (1H, exch D2O), 9.51 (1H, s, exch D2O); HPLC/MS retention time 4.29 min, m/z 368 (MH+).

Workup

  1. customThe solution was evaporated to dryness
  2. dissolutionthe resulting gum was redissolved on methanol (10 ml)
  3. additioncontaining 5% Pd—C (60 mg)
  4. stirringThe mixture was stirred under an atmosphere of hydrogen for 2 hours
  5. customThe catalyst was removed by filtration
  6. customthe filtrate evaporated to dryness
  7. customgiving a gum

Sources & evidence

ORD record
ord-9e22515780bd4900b8ad2f86d07758c9
Source dataset
uspto-grants-2012_09
Patent number
US08258097B2

Reaction notes

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