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2,4,5-Trichlorophenol → t-Butoxycarbonyl-glycyl-glycine-2,4,5-Trichlorophenyl Ester

HRID 1863468
Notes
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Reaction equation

HRID 1863468 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][CH2:13][C:14]([OH:16])=[O:15])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=1O.ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[CH:20][C:19]=1[O:15][C:14](=[O:16])[CH2:13][NH:12][C:10](=[O:11])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 72712,4,5-TrichlorophenolHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 3334662-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)acetic acid

Product 1

HCID 54236985t-Butoxycarbonyl-glycyl-glycine-2,4,5-Trichlorophenyl Ester

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

Dissolve 2.5 g. of t-butoxycarbonyl-glycyl-glycine in dimethylformamide (20 ml.) containing 2,4,5-trichlorophenol (2.13 g.) and N-hydroxysuccinimide (1.4 g.) . Cool the solution in an ice bath and stir while adding dicyclohexylcarbodiimide (2.44 g.) in dimethylformamide (5 ml.). Allow the reaction mixture to stand at room temperature for 48 hours, filter the reaction mixture and evaporate the filtrate to dryness under reduced pressure. Chromatograh the residue on silica gel (150 g.). The desired product is eluted with 20% ethyl acetate/chloroform and crystallized from ether-hexane (m.p. 90°-91° C.).

Workup

  1. dissolutionDissolve 2.5 g
  2. temperatureCool the solution in an ice bath
  3. filtrationfilter the reaction mixture
  4. customevaporate the filtrate to dryness under reduced pressure
  5. washThe desired product is eluted with 20% ethyl acetate/chloroform
  6. customcrystallized from ether-hexane (m.p. 90°-91° C.)

Sources & evidence

ORD record
ord-d64d82f187924feba5b56358f4884c95
Source dataset
uspto-grants-1979_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04169141

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes