di-tert-butyl 4-(4-hydroxybenzyl)-L-glutamate → (4R)-4-(4-hydroxybenzyl)-L-glutamic acid

HRID 591333Notes

Reaction equation

HRID 591333 reaction equation
[OH:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][CH:7]([C:18]([O:20]C(C)(C)C)=[O:19])[CH2:8][C@@H:9]([C:11]([O:13]C(C)(C)C)=[O:12])[NH2:10])=[CH:4][CH:3]=1>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@H:7]([C:18]([OH:20])=[O:19])[CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:25][CH:26]=1

Participants

4

Reactant 1

HCID 70977414di-tert-butyl 4-(4-hydroxybenzyl)-L-glutamate

Product 1

HCID 70977181(4R)-4-(4-hydroxybenzyl)-L-glutamic acid

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Di-tert-butyl 4-(4-hydroxybenzyl)-L-glutamate (27 mg, 58 μmol) was dissolved in trifluoroacetic acid (1 ml) and stirred at room temperature for 2 h. The mixture was then taken up in toluene and concentrated under reduced pressure. The residue was purified by preparative HPLC (RP-18; solvents: acetonitrile (+0.1% trifluoroacetic acid), water (+0.1% trifluoroacetic acid); gradient: 30%->40% acetonitrile (20 min)).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by preparative HPLC (RP-18; solvents: acetonitrile (+0.1% trifluoroacetic acid), water (+0.1% trifluoroacetic acid); gradient: 30%->40% acetonitrile (20 min))

Sources & evidence

ORD record
ord-fd7030a20eb14ff5b7b5b239a4e945e2
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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