Dicyclohexylcarbodiimide → HCID 131711090, compound

HRID 2083838Notes

Reaction equation

HRID 2083838 reaction equation
[CH3:1][O:2][C:3](=[O:53])[C@H:4]([CH2:49][CH:50]([CH3:52])[CH3:51])[NH:5][C:6](=[O:48])[C@@H:7]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[NH:8][C:9](=[O:40])[C@H:10]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[NH:11][C:12](=[O:31])[C@H:13]([CH2:29][OH:30])[NH:14][C:15](=[O:28])[C@H:16]([CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[NH2:17].[CH3:54][O:55][C:56]1[CH:79]=[CH:78][C:59]([CH2:60][O:61][C:62]([NH:64][C@H:65]([C:75](O)=[O:76])[CH2:66][O:67][CH2:68][C:69]2[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=2)=[O:63])=[CH:58][CH:57]=1.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:53])[C@H:4]([CH2:49][CH:50]([CH3:51])[CH3:52])[NH:5][C:6](=[O:48])[C@@H:7]([CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[NH:8][C:9](=[O:40])[C@H:10]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[NH:11][C:12](=[O:31])[C@H:13]([CH2:29][OH:30])[NH:14][C:15](=[O:28])[C@H:16]([CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)[NH:17][C:75](=[O:76])[C@H:65]([CH2:66][O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)[NH:64][C:62]([O:61][CH2:60][C:59]1[CH:78]=[CH:79][C:56]([O:55][CH3:54])=[CH:57][CH:58]=1)=[O:63]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 12764079HCID 12764079, compoundHCID 54560982HCID 54560982, compound

Product 1

HCID 131711090HCID 131711090, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-Tryptophyl-L-seryl-L-tyrosyl-D-phenylalanyl-L-leucine methyl ester (example 1, h), 1.6 g., is dissolved in 30 ml. of dimethylformamide and treated with 0.789 g., of Nα -p-methoxybenzyloxycarbonyl-O-benzyl-L-serine and cooled in an ice bath. 1-Hydroxybenzotriazole, 326 mg., and finally 500 mg., of dicyclohexylcarbodiimide are added and the reaction mixture stirred to room temperature overnight and for twenty-four additional hours. The reaction mixture is filtered and the solvent removed under reduced pressure. The residue is dissolved in 200 ml. of ethyl acetate and washed with 0.25 N hydrochloric acid, saturated sodium chloride solution, 5% sodium bicarbonate solution, and finally, saturated sodium chloride solution. The ethyl acetate solution is refrigerated for several days and a gelatinous precipitate separated. After triturating with ether for two hours, the above named product is separated and dried, 1.7 g.

Workup

  1. dissolution, is dissolved in 30 ml
  2. filtrationThe reaction mixture is filtered
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe residue is dissolved in 200 ml
  5. washof ethyl acetate and washed with 0.25 N hydrochloric acid, saturated sodium chloride solution, 5% sodium bicarbonate solution
  6. waitThe ethyl acetate solution is refrigerated for several days
  7. customa gelatinous precipitate separated
  8. customAfter triturating with ether for two hours
  9. customthe above named product is separated
  10. customdried

Sources & evidence

ORD record
ord-eb14355f7bc949e190d6b0606657f50b
Source dataset
uspto-grants-1978_04
Patent number
US04086219

Reaction notes

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