Dicyclohexylcarbodiimide → HCID 86735999, compound

HRID 1763735Notes

Reaction equation

HRID 1763735 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].[C:54]([O:58][C:59]([NH:61][C@H:62]([C:72]([OH:74])=O)[CH2:63][O:64][CH2:65][C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1)=[O:60])([CH3:57])(C)C.ON1[C:80]2C=CC=C[C:79]=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:72](=[O:74])[C@H:62]([CH2:63][O:64][CH2:65][C:66]1[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=1)[NH:61][C:59]([O:58][CH2:54][CH2:57][CH2:79][CH3:80])=[O:60]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 54560982HCID 54560982, compound

Product 1

HCID 86735999HCID 86735999, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-Tryptophyl-L-seryl-L-tyrosyl-D-phenylalanyl-L-leucine methyl ester, 1.53 g., is dissolved in 35 ml. of dimethylformamide, the solution cooled in ice and treated with 620 mg. of Nα -t-butoxycarbonyl-O-benzyl-L-serine, 311 mg. of 1-hydroxybenztriazole and 475 mg. of dicyclohexylcarbodiimide (10% excess). The reaction is stirred overnight to room temperature and twenty-four hours additional at room temperature. The mixture is filtered and the filtrate evaporated under reduced pressure. The residue is dissolved in 500 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 and evaporated. The residual solid is dried under reduced pressure; 2.29 g.; m.p. 200°-202° C.; [α]D23 -19.5° (c 1.03, methanol); ultraviolet in methanol λmax 289.5 E11 52; λmax 280 E11 68.

Workup

  1. dissolution, is dissolved in 35 ml
  2. additiontreated with 620 mg
  3. filtrationThe mixture is filtered
  4. customthe filtrate evaporated under reduced pressure
  5. dissolutionThe residue is dissolved in 500 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. customevaporated
  9. customThe residual solid is dried under reduced pressure

Sources & evidence

ORD record
ord-b7d25f8b897145bfadb26f2390a8d3ba
Source dataset
uspto-grants-1978_09
Patent number
US04111923

Reaction notes

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