Pentachlorophenol → N2-Benzyl pentachlorophenyl N2-carboxy-L-(2-aminoglutaramate)

HRID 1578538Notes

Reaction equation

HRID 1578538 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][C:15](=[O:17])[NH2:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:21][C:22]1[C:27](O)=[C:26]([Cl:29])[C:25]([Cl:30])=[C:24]([Cl:31])[C:23]=1[Cl:32].C1C=C(SSC2N=CC=CC=2)N=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(C)=O>[Cl:21][C:22]1[C:27]([O:19][C:18](=[O:20])[C@H:12]([CH2:13][CH2:14][C:15](=[O:17])[NH2:16])[NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])=[C:26]([Cl:29])[C:25]([Cl:30])=[C:24]([Cl:31])[C:23]=1[Cl:32]

Participants

6

Reactant 4

HCID 992PentachlorophenolHCID 11776TriphenylphosphineHCID 650932,2'-Dipyridyl disulfideHCID 75855L-Glutamine, N2-[(phenylmethoxy)carbonyl]-

Product 1

HCID 117402N2-Benzyl pentachlorophenyl N2-carboxy-L-(2-aminoglutaramate)

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 0.700 g. of N-benzyloxycarbonyl-L-glutamine, 0.665 g. of pentachlorophenol and 0.55 g. of 2,2'-dipyridyl disulfide in 20 ml. of dry acetone is added an acetone solution of 0.655 g. of triphenyl phosphine with stirring at 0°C. The produced precipitates are recovered by filtration and washed successively with a 3 % sodium bicarbonate solution, water and ether and recrystallized from a mixture of dimethylformamide and methanol to give 0.952 g. of the desired product.

Workup

  1. customThe produced precipitates
  2. filtrationare recovered by filtration
  3. washwashed successively with a 3 % sodium bicarbonate solution, water and ether
  4. customrecrystallized from a mixture of dimethylformamide and methanol
  5. customto give 0.952 g

Sources & evidence

ORD record
ord-0f56f22f8cf24f908a556e093ccbede6
Source dataset
uspto-grants-1976_02
Patent number
US03937718

Reaction notes

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