1-Hydroxybenzotriazole → HCID 12807303, compound

HRID 256492Notes

Reaction equation

HRID 256492 reaction equation
[NH2:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl.[NH:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:10]([C:14](O)=[O:15])[CH:11]([CH3:13])[CH3:12].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[NH:9]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[C@H:10]([C:14]([NH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:15])[CH:11]([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-ValineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 12807303HCID 12807303, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of 3.21 g of the H-Gly-OEt.HCl dissolved in 10 ml of DMF, under cooling at -5° C., 5.00 g of Boc-Val-OH, 3.10 g of HOBT and 4.79 g of WSC.HCl were added, and the mixture was stirred at -5° C. for one hour and at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate, successively washed three times with 1N hydrochloric acid, once with saturated aqueous sodium chloride, three times with 5% aqueous sodium hydrogen carbonate, three times with saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was recrystallized from ethyl acetate-n-hexane to give 5.93 g (yield: 85.2%) of Boc-Val-Gly-OEt melting at 91.5° to 93° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washsuccessively washed three times with 1N hydrochloric acid
  4. dry with materialonce with saturated aqueous sodium chloride, three times with 5% aqueous sodium hydrogen carbonate, three times with saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-36c498b4fc154cc8999156e4508253f2
Source dataset
uspto-grants-1987_10
Patent number
US04703106

Reaction notes

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