tert-Butanol → Boc-L-phenylalanine methyl ester

HRID 2271246Notes

Reaction equation

HRID 2271246 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[N:5]=[C:6]=[O:7].[C:16]([OH:20])([CH3:19])([CH3:18])[CH3:17]>>[CH3:1][O:2][C:3](=[O:15])[C@H:4]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[NH:5][C:6]([O:20][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:7]

Participants

3

Reactant 2

HCID 6386tert-ButanolHCID 1514293Methyl N-(oxomethylidene)phenylalaninate

Product 1

HCID 9882138Boc-L-phenylalanine methyl esterYield 99.5%

Procedure

To 60.9 g of the N-carbonyl-L-phenylalanine methyl ester, 66.0 g of t-butanol was added and the reaction was conducted under reflux for eight hours. Then, the unreacted t-butanol was distilled off at 65° C. under reduced pressure from the reaction solution to obtain 82.5 g of a crude oily N-t-butoxycarbonyl-L-phenylalanine methyl ester. The reaction yield was 99.5%. The optical purity of the N-t-butoxycarbonyl-L-phenylalanine methyl ester preparation was 97.5%ee.

Workup

  1. temperatureunder reflux for eight hours
  2. distillationThen, the unreacted t-butanol was distilled off at 65° C. under reduced pressure from the reaction solution

Sources & evidence

ORD record
ord-b00aaaf4d0854ceabac7ea22939103d5
Source dataset
uspto-grants-2001_12
Patent number
US06333427B1

Reaction notes

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