Dicyclohexylcarbodiimide → Fmoc-Tyr(tBu)-Cys(Trt)-Asn-OtBu

HRID 2210910Notes

Reaction equation

HRID 2210910 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[NH:16]([C:33]([O:35][CH2:36][CH:37]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:34])[C@H:17]([C:30](O)=[O:31])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:21][CH:20]=1.[NH2:50][C@H:51]([C:73]([NH:75][C@H:76]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[CH2:77][C:78](=[O:80])[NH2:79])=[O:74])[CH2:52][S:53][C:54]([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)([C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[NH:16]([C:33]([O:35][CH2:36][CH:37]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)=[O:34])[C@H:17]([C:30]([NH:50][C@H:51]([C:73]([NH:75][C@H:76]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[CH2:77][C:78](=[O:80])[NH2:79])=[O:74])[CH2:52][S:53][C:54]([C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1)([C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)=[O:31])[CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]([CH3:28])([CH3:27])[CH3:29])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10895791Fmoc-L-Tyr(tBu)-OHHCID 131719153HCID 131719153, compound

Product 1

HCID 131719152Fmoc-Tyr(tBu)-Cys(Trt)-Asn-OtBu

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1.63 g of DCC are added to a stirred solution of 3.4 g of Fmoc-Tyr(tBu)-OH, 3.95 g (7.4 mmol) of H-Cys(Trt)-Asn-OtBu (Liebigs Ann. Chem. 1979, 242) and 1 g of HOBT in 50 ml of dimethylformamide at 0° C., and the mixture is left to stir at 0° C. for 1 h and to stand at room temperature overnight. The next day, the precipitate is filtered off with suction and the filtrate is concentrated. The residue is triturated with ethyl acetate. Yield 2.83 g. A further 3.63 g can be isolated from the mother liquor. Total yield: 6.46 g (89%).

Workup

  1. waitthe mixture is left
  2. waitto stand at room temperature overnight
  3. filtrationThe next day, the precipitate is filtered off with suction
  4. concentrationthe filtrate is concentrated
  5. customThe residue is triturated with ethyl acetate
  6. customA further 3.63 g can be isolated from the mother liquor

Sources & evidence

ORD record
ord-f55ddd1e68f5410b967525c391c86148
Source dataset
uspto-grants-1995_10
Patent number
US05461035

Reaction notes

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