Dicyclohexylcarbodiimide → HCID 54357846, compound

HRID 2082116Notes

Reaction equation

HRID 2082116 reaction equation
[C:1]([S:9][CH2:10][C:11]([NH:13][CH2:14][C:15]([NH:17][C@@H:18]([C:20]([OH:22])=O)[CH3:19])=[O:16])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([O:25][C:26](=[O:29])[CH2:27][NH2:28])[CH3:24].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH2:23]([O:25][C:26](=[O:29])[CH2:27][NH:28][C:20](=[O:22])[C@@H:18]([CH3:19])[NH:17][C:15](=[O:16])[CH2:14][NH:13][C:11](=[O:12])[CH2:10][S:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:24]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 12176Glycine ethyl esterHCID 53778955HCID 53778955, compound

Product 1

HCID 54357846HCID 54357846, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Benzoylmercaptoacetylglycyl-D-alanine in an amount of 150 mg is dissolved in 40 ml of tetrahydrofuran and the solution is cooled in an ice bath at 0° C. A solution of 50 mg of glycine-ethyl ester and 100 mg of dicyclohexylcarbodiimide in 15 ml of tetrahydrofuran is slowly added while stirring magnetically. The mixture is stirred at 0° C. for 2 hours and then at room temperature for 15 hours. The resulting precipitate is then filtered off and the filtrate is evaporated to dryness under reduced pressure. The solid residue is shaken with a mixture of 50 ml of water and 50 ml of methylene chloride. The organic layer is separated, dried over anhydrous sodium sulphate and evaporated to dryness in vacuo. The solid residue is shaken five times with 15 ml of acetone which is each time filtered off. The collected filtrates are concentrated in vacuo to 15 ml and diethylether is added dropwise thereto while stirring until complete formation of precipitate. The precipitate is filtered off, washed with diethyl ether and dried over phosphorous pentoxide in vacuo. In this manner, 155 mg (55.1% yield) of benzoylmercaptoacetylglycyl-D-alanylglycine ethyl ester are obtained. The identity of this compound is confirmed by mass spectrometry, proton-NMR analysis and elementary analysis: mp 137° C.; [α]D20 +20.5 (C=1 in methanol); mass spectrum m/e- 410; nmr (DMSO-d6): δ1.22 (3H, d, CH3), 3.77 (2H, d, γ--CH2 --N), 3.81 (2 H, d, α--CH2 --N), 3.87 (2H, s, CH2 --S), 4.33 (1H, q, β--CH), 8.08 (1H, d, β--NH), 8.28 (1H, t, α--NH), 8.42 (1H, t, γ--NH), 7.5-8.04 (5H, complex, aromatic), 4.08 (2H, q, OCH2), 1.18 (3H, t, ester-CH3).

Workup

  1. stirringThe mixture is stirred at 0° C. for 2 hours
  2. filtrationThe resulting precipitate is then filtered off
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. stirringThe solid residue is shaken with a mixture of 50 ml of water and 50 ml of methylene chloride
  5. customThe organic layer is separated
  6. dry with materialdried over anhydrous sodium sulphate
  7. customevaporated to dryness in vacuo
  8. stirringThe solid residue is shaken five times with 15 ml of acetone which
  9. filtrationfiltered off
  10. concentrationThe collected filtrates are concentrated in vacuo to 15 ml and diethylether
  11. additionis added dropwise
  12. stirringwhile stirring until complete formation of precipitate
  13. filtrationThe precipitate is filtered off
  14. washwashed with diethyl ether
  15. dry with materialdried over phosphorous pentoxide in vacuo

Sources & evidence

ORD record
ord-c64e6ec089ae40548be89259dba1e5e3
Source dataset
uspto-grants-1993_02
Patent number
US05187264

Reaction notes

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