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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Z-Ser-Tyr-OMe

HRID 1279182
Notes
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Reaction equation

HRID 1279182 reaction equation
[NH:1]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C@H:2]([C:5]([OH:7])=O)[CH2:3][OH:4].[NH2:18][C@H:19]([C:28]([O:30][CH3:31])=[O:29])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1.ON1C(=O)CCC1=O.CCN=C=NCCCN(C)C>CN(C=O)C>[NH:1]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C@H:2]([C:5]([NH:18][C@H:19]([C:28]([O:30][CH3:31])=[O:29])[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)=[O:7])[CH2:3][OH:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70652Tyrosine Methyl EsterHCID 80170N-HydroxysuccinimideHCID 100310N-(Benzyloxycarbonyl)-L-serine

Product 1

HCID 13190522Z-Ser-Tyr-OMeYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
0 °C

Procedure

Z-Ser-OH 23.9 g and 23.2 g of H-Tyr-OMe were dissolved in 50 mL of DMF, 12.7 g of HOSu and 20 mL of WSC were added to the solution, then the mixture was stirred at 0° C. for 5 minutes then at room temperature overnight. After confirmation with ninhydrin, the reaction mixture was concentrated under reduced pressure. Ethyl acetate 500 mL was added to the residue, and the mixture was washed twice with 200 mL of 1N hydrochloric acid, twice with 200 mL of saturated aqueous sodium bicarbonate, twice with saturated saline, in this order. The ethyl acetate layer was concentrated under reduced pressure. The residue was solidified by treatment with hexane. Thus 38.44 g of Z-Ser-Tyr-OMe (92.3% yield) was obtained.

Workup

  1. customat room temperature
  2. customovernight
  3. concentrationAfter confirmation with ninhydrin, the reaction mixture was concentrated under reduced pressure
  4. additionEthyl acetate 500 mL was added to the residue
  5. washthe mixture was washed twice with 200 mL of 1N hydrochloric acid, twice with 200 mL of saturated aqueous sodium bicarbonate, twice with saturated saline, in this order
  6. concentrationThe ethyl acetate layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4dc8528b1e4d48c89102bfc4c191e200
Source dataset
uspto-grants-2002_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06448031B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes