Methyl Methacrylate → HCID 69287551, compound

HRID 1393263Notes

Reaction equation

HRID 1393263 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([PH:17](=[O:19])[OH:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N([Si](C)(C)C)[Si](C)(C)C.[C:29]([O:34][CH3:35])(=[O:33])[C:30]([CH3:32])=[CH2:31]>CCO>[CH3:35][O:34][C:29](=[O:33])[CH:30]([CH3:32])[CH2:31][P:17]([C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([OH:18])=[O:19]

Participants

5

Reactant 3

HCID 6658Methyl MethacrylateHCID 13838HexamethyldisilazaneHCID 178454161HCID 178454161, compound

Product 1

HCID 69287551HCID 69287551, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5.00 g of ((R)-1-tert-butoxycarbonylamino-2-phenyl-ethyl)-phosphinic acid and 18.3 ml of HN(TMS)2 was heated to 110° C. for 1 h. To the solution was added 2.5 ml of methyl methacrylate and heating was continued at 110° C. for 2 h. The solution was cooled to 70° slowly diluted with 10 ml of EtOH and evaporated. The residue was chromatographed on silica using a gradient of CH2Cl2/MeOH (9:1)→CH2Cl2/MeOH/AcOH (10:1:0.3) to give 4.10 g of the title compound. MS: 386.5 (M+H)+.

Workup

  1. temperatureheating
  2. temperatureThe solution was cooled to 70°
  3. customevaporated
  4. customThe residue was chromatographed on silica using a gradient of CH2Cl2/MeOH (9:1)→CH2Cl2/MeOH/AcOH (10:1:0.3)

Sources & evidence

ORD record
ord-cb46db7d34ba4df5adb31e0509f5af2b
Source dataset
uspto-grants-2008_03
Patent number
US07345082B2

Reaction notes

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