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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → BOC-Leu-Gly-OBzl

HRID 256496
Notes
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Reaction equation

HRID 256496 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].O.C1C=CC2N(O)N=NC=2C=1.CC1C=CC(S(O)(=O)=O)=CC=1.[CH:39]1[CH:44]=[CH:43][C:42]([CH2:45][O:46][C:47]([CH2:49][NH2:50])=[O:48])=[CH:41][CH:40]=1.CCN=C=NCCCN(C)C>CN(C=O)C>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([NH:50][CH2:49][C:47]([O:46][CH2:45][C:42]1[CH:43]=[CH:44][CH:39]=[CH:40][CH:41]=1)=[O:48])=[O:9])[CH2:3][CH:4]([CH3:5])[CH3:6]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 12373896N-Boc-L-Leucine Hydrate

Product 1

HCID 13242213BOC-Leu-Gly-OBzl

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Conditions

Temperature
-5 °C

Procedure

To a solution of 6.00 g of BOC-Leu-OH.H2O, 3.49 g of HOBT and 9.59 of H-Gly-OBzl.TosOH dissolved in 30 ml of DMF, under cooling at -5° C. and stirring, a solution of 4.97 ml of WSC dissolved in 10 ml of DMF was added dropwise, and after one hour, the temperature was regulated to room temperature, at which stirring was continued overnight. The reaction mixture was concentrated under reduced pressure to evaporate DMF, and the residue was dissolved in ethyl acetate. The ethyl acetate layer was washed successively with 1N hydrochloric acid, water, 5% aqueous sodium hydrogen carbonate and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 9.2 g of BOC-Leu-Gly-OBzl as oily product. Rf1 =0.59.

Workup

  1. additionwas added dropwise
  2. customwas regulated to room temperature, at which
  3. stirringstirring
  4. waitwas continued overnight
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customto evaporate DMF
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washThe ethyl acetate layer was washed successively with 1N hydrochloric acid, water, 5% aqueous sodium hydrogen carbonate and water
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f8afd9897194a1885a558ecbd9bcb00
Source dataset
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04703106

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes