L-Tyrosine → HCID 11439483, compound

HRID 1805404Notes

Reaction equation

HRID 1805404 reaction equation
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16]>[OH-].[Na+]>[C:15]([O:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][C@@H:2]([C:11]([OH:13])=[O:12])[NH:1][C:15]([O:17][CH2:18][CH:19]=[CH2:20])=[O:16])=[CH:9][CH:8]=1)([O:17][CH2:18][CH:19]=[CH2:20])=[O:16]

Participants

4

Reactant 2

HCID 6057L-Tyrosine2×HCID 18052Allyl chloroformate2×

Product 1

HCID 11439483HCID 11439483, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

The first step (a) is the bis-protection of tyrosine amino acid using allyl chloroformate, as described in Stevens, C. M. and Watanabe, R., J. Am. Chem. Soc., 1950, 72, 725-727 (FIG. 11A). Tyrosine (n=0.03 mol, m=5.44 g) is dissolved in 15 ml of 4N sodium hydroxide and treated, when cold, with 7.02 ml (2.2 equiv.) of allyl chloroformate and additional 15 ml of 4N sodium hydroxide. After treatment and purification, O,N-dicarboallyloxy-L-tyrosine is obtained in 89% yield (Litt. 91%) as a crystalline derivative.

Workup

  1. additiontreated
  2. customAfter treatment and purification

Sources & evidence

ORD record
ord-126018c60329497a83d616ce1524bb2e
Source dataset
uspto-grants-2013_01
Patent number
US08354498B2

Reaction notes

Loading…