Dimethylformamide → HCID 13647094, compound

HRID 1763732Notes

Reaction equation

HRID 1763732 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:20]([OH:22])=O)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:24][O:25][C:26](=[O:33])[C@H:27]([CH2:29][CH:30]([CH3:32])[CH3:31])[NH2:28].CN(C)C=O.C1(N=C=NC2CCCCC2)CCCCC1>C(N(CC)CC)C>[CH3:24][O:25][C:26](=[O:33])[C@H:27]([CH2:29][CH:30]([CH3:32])[CH3:31])[NH:28][C:20](=[O:22])[C@@H:12]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 675678N-(Benzyloxycarbonyl)-D-phenylalanineHCID 2723695Leucine methyl ester hydrochloride

Product 1

HCID 13647094HCID 13647094, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 6.65 g. of Nα -benzyloxycarbonyl-D-phenylalanine (0.022 mol) and 4.38 g. (0.022 mol) of L-leucine methyl ester hydrochloride in 60 ml. of spectrograde dimethylformamide is chilled in ice and treated with 3.0 ml. of triethylamine (2.24 g.). 1-Hydroxybentriazole, 3.3 g., and dicyclohexylcarbodiimide, 5 g., are added and the reaction stirred at room temperature overnight and for 24 hours longer at room temperature. The mixture is filtered and the solvent evaporated under reduced pressure. The residue is dissolved in 200 ml. of ethyl acetate and washed with 0.1N hydrochloric acid, saturated salt solution, 5% sodium bicarbonate solution, saturated salt solution and water. The ethyl acetate solution is dried over magnesium sulfate, filtered and evaporated to a crystalline residue. The product is recrystallized twice from ethyl acetate and petroleum ether; 7.3 g.; m.p. 125°-126° C.; [α]D23 -20.3° (c 1.02, methanol).

Workup

  1. additiontreated with 3.0 ml
  2. addition, are added
  3. filtrationThe mixture is filtered
  4. customthe solvent evaporated under reduced pressure
  5. dissolutionThe residue is dissolved in 200 ml
  6. washof ethyl acetate and washed with 0.1N hydrochloric acid, saturated salt solution, 5% sodium bicarbonate solution, saturated salt solution and water
  7. dry with materialThe ethyl acetate solution is dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to a crystalline residue
  10. customThe product is recrystallized twice from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-85c781e6fdf24c4a85722b2bbb014b98
Source dataset
uspto-grants-1978_09
Patent number
US04111923

Reaction notes

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