Toluene → HCID 131717576, compound

HRID 466231Notes

Reaction equation

HRID 466231 reaction equation
[P:1]([CH2:5][NH:6][CH:7]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])([OH:4])([OH:3])=[O:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:41]([O:47][CH2:48]I)(=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43].[C:50]([O:53][CH2:54]C)(=[O:52])C.[C:56]1([CH3:62])[CH:61]=CC=C[CH:57]=1>>[C:41]([O:47][CH2:48][C:5]([CH2:54][O:53][C:50](=[O:52])[C:56]([CH3:57])([CH3:61])[CH3:62])([NH:6][CH:7]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:21][CH:20]=1)[C:8]([NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])[P:1]([OH:4])([OH:3])=[O:2])(=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 5

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 104401Iodomethyl pivalateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 10003027HCID 10003027, compound

Product 1

HCID 131717576HCID 131717576, compound

Procedure

A solution of ethyl N-[2-(phosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionate (0.3 g, 0.69 mmol), 18 crown-6 (0.36 g, 1.38 mmol) in toluene (12 mL) is cooled to 0° and is treated with potassium bis-trimethylsilylamide (2.22 mL, 1.45 mmol). After 7 minutes the clear solution is treated with iodomethyl pivalate (0.25 mL, 1.56 mmol) and stirred for 18 hours. Ethyl acetate is added, the mixture is washed with water, dried (Na2SO4), concentrated and the residue is chromatographed on silica gel (EtOAc/hexanes, 75:25) to obtain ethyl N-{2-[di-(pivaloyloxymethyl)-phosphonomethylamino]-3-(4-biphenylyl)propionyl}-3-aminopropionate as an oil.

Workup

  1. washthe mixture is washed with water
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customthe residue is chromatographed on silica gel (EtOAc/hexanes, 75:25)

Sources & evidence

ORD record
ord-0659512301ee4bf89ad7fba196635124
Source dataset
uspto-grants-1992_10
Patent number
US05155100

Reaction notes

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