Ethanol → HCID 15021432, compound

HRID 1461621Notes

Reaction equation

HRID 1461621 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:18]([O:20][CH3:21])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:22][C:23]1([CH3:27])[O:26][CH:24]1C.CCO>C(Cl)Cl>[CH3:21][O:20][C:18](=[O:19])[C@H:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[NH:12][C:10](=[O:11])[C@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH:1][CH2:22][C:23]([OH:26])([CH3:27])[CH3:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 21158TrimethyloxiraneHCID 7370972HCID 7370972, compound

Product 1

HCID 15021432HCID 15021432, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Phe-Leu-OMe (0.69 mmol) in CH2Cl2 (1 mL) was added dimethyl propylene oxide (0.075 mL). The reaction mixture was stirred at room temperature overnight, however, no change was observed. Two additional mLs of the oxide were added and then the reaction mixture was transferred with EtOH (excess) to a closed tube reactor, heated to 100° C. for 5 hours, stirred at room temperature for 2 days, and concentrated to yield 0.24 g of N-(2-hydroxy-2-methylpropyl)-L-phenylalanyl-L-leucine methyl ester.

Workup

  1. temperatureheated to 100° C. for 5 hours
  2. stirringstirred at room temperature for 2 days
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b891b517342a4e8db56039479894ad8e
Source dataset
uspto-grants-1991_12
Patent number
US05075451

Reaction notes

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