L-Pyroglutamic Acid → L-Pyroglutamic Acid

HRID 890346Notes

Reaction equation

HRID 890346 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].[CH2:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:18]=[CH:19][CH:20]=[CH2:21].CN(CCN(C)C)C.[Li]CCCC>CCCCCC>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=[O:8].[CH2:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:18]=[CH:19][CH:20]=[CH2:21]

Participants

8

Reactant 5

HCID 7405L-Pyroglutamic Acid2×HCID 7501Styrene2×HCID 78451,3-ButadieneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 178418339Butyllithium

Product 2

HCID 7405L-Pyroglutamic AcidHCID 62697Benzene, ethenyl-, polymer with 1,3-butadiene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In this experiment, a 0.5/19.5/80 Pyr-AMS/styrene/1,3-butadiene terpolymer was prepared. The procedure described in Example 1 was used except that a premix containing Pyr-AMS, styrene and 1,3-butadiene in hexane at a weight ratio of 0.5:19.5:80 was used as the monomer premix solution and the molar ratio of potassium 3,7-dimethyl-3-octanoxide to TMEDA to n-BuLi was 0.015:2:1. The GC analysis of residual monomer again showed that polymerization rates of the three monomers were almost identical indicating that both Pyr-AMS and styrene were randomly distributed along the polymer chain.

Workup

  1. additionpremix solution
  2. customThe GC analysis of residual monomer again showed that polymerization rates of the three monomers

Sources & evidence

ORD record
ord-a5202667093b43e09264a3435fea2fa2
Source dataset
uspto-grants-2006_02
Patent number
US06995224B2

Reaction notes

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