Methanol → HCID 22869565, compound

HRID 1449692Notes

Reaction equation

HRID 1449692 reaction equation
[C:1]([O-:4])([O-:3])=O.[K+].[K+].C(N[C:15](=[O:29])[C@H:16]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]=[CH2:28])=[CH:21][CH:20]=1)[NH2:17])(OC(C)(C)C)=O.[CH3:30][OH:31]>>[CH3:30][O:31][C:15](=[O:29])[C@H:16]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH:27]=[CH2:28])=[CH:23][CH:24]=1)[NH:17][C:1]([O:4][C:19]([CH3:24])([CH3:20])[CH3:18])=[O:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86750268HCID 86750268, compound

Product 1

HCID 22869565HCID 22869565, compoundYield 92%

Procedure

K2CO3 (20 mg, 0.145 mmol) was added to a stirred solution of 3 (100 mg, 0.131 mmol) in CH3OH (2 mL). After 30 min, the reaction mixture was filtered, diluted with ether (10 mL), and washed with aq NH4Cl and brine. Concentration followed by flash chromatography (20% diethyl ether/pentane) afforded N-Boc-O-allyltyrosine methyl ester (40.0 mg, 92%).

Workup

  1. filtrationthe reaction mixture was filtered
  2. additiondiluted with ether (10 mL)
  3. washwashed with aq NH4Cl and brine
  4. concentrationConcentration

Sources & evidence

ORD record
ord-7ff9e55c066a4b99857a7677441da694
Source dataset
uspto-grants-1997_02
Patent number
US05599926

Reaction notes

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