Ethyl Acetate → HCID 54173961, compound

HRID 2298253Notes

Reaction equation

HRID 2298253 reaction equation
[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[NH:5][C:6](=[O:22])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13].[H-].[Na+].CC[O:36][C:37]([CH3:39])=[O:38]>>[CH3:1][O:2][C:3](=[O:31])[C@H:4]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:6]2[CH:7]=[CH:11][CH:10]=[CH:9][C:39]=2[C:37]([OH:36])=[O:38])=[CH:26][CH:25]=1)[NH:5][C:6](=[O:22])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:13])=[O:14]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 54334627HCID 54334627, compound

Product 1

HCID 54173961HCID 54173961, compound

Procedure

N-(Toluene-4-sulfonyl)-L-prolyl-L-tyrosine methyl ester (2.14 g, 5.16 mmol) was added to a suspension of sodium hydride (60% in oil, 1.1 eq, 228 mg) in xylenes (50 mL) at 0° C. The reaction mixture was stirred for 5 minutes and cuprous bromideodimethyl sulfide complex (1.4 eq, 1.48 g) was added. The reaction mixture was stirred at 23° C. for 0.5 hours. 2-Iodo sodium benzoate (1.5 eq, 8.06 mmol) was added and the reaction mixture was refluxed for 12 hours. EtOAc (100 mL) was added, and the organic layer washed with NH4Cl, 10% HCl, and brine, dried over MgSO4. The crude material was eluted on column chromatography (silica gel), with CHCl3:MeOH 9:1, and the title compound was isolated as an oil.

Workup

  1. additioncuprous bromideodimethyl sulfide complex (1.4 eq, 1.48 g) was added
  2. stirringThe reaction mixture was stirred at 23° C. for 0.5 hours
  3. temperaturethe reaction mixture was refluxed for 12 hours
  4. washthe organic layer washed with NH4Cl, 10% HCl, and brine
  5. dry with materialdried over MgSO4
  6. washThe crude material was eluted on column chromatography (silica gel), with CHCl3:MeOH 9:1

Sources & evidence

ORD record
ord-21a66136071340ef9e720b594268494f
Source dataset
uspto-grants-2002_12
Patent number
US06492421B1

Reaction notes

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