Dicyclohexylcarbodiimide → HCID 131717181, compound

HRID 1534894Notes

Reaction equation

HRID 1534894 reaction equation
[NH:1]([C:16]([O:18][CH2:19][CH:20]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[C@@H:2]([C:13]([OH:15])=O)[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH2:33][C@H:34]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:35][O:36][C:37]([CH3:40])([CH3:39])[CH3:38].Cl.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C=O.C(N1CCOCC1)C>[NH:1]([C:16]([O:18][CH2:19][CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]2[C:32]1=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:17])[C@@H:2]([C:13]([NH:33][C@H:34]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:35][O:36][C:37]([CH3:40])([CH3:38])[CH3:39])=[O:15])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 97834486123-11-7HCID 16211506H-Ser(tBu)-OtBu HCl

Product 1

HCID 131717181HCID 131717181, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7525EthylmorpholineSolvent

Procedure

To a solution ob 17.1 g (40 mmol) of Fmoc-D-Trp-OH, 10.12 g of H-Ser(tBu)-OtBu.HCl and 5.4 g of HOBt in 100 ml of dimethylformamide, 5.2 ml of N-ethylmorpholine are added at 0° C. with stirring, followed by 8.8 g of DCC. After allowing to stir for 1 hour at 0° C. and 3 hours at room temperature, the precipitate is filtered off with suction and the filtrate is concentrated in vacuo. The residue is dissolved in ethyl acetate and washed successively with water, saturated NaHCO3 solution and water, dried over Na2SO4 and concentrated in vacuo. The solution of the resulting oil in 70 ml of diethyl ether is dropper with stirring into 700 ml of petroleum ether. The precipitate is filtered off with suction and dried.

Workup

  1. stirringto stir for 1 hour at 0° C. and 3 hours at room temperature
  2. filtrationthe precipitate is filtered off with suction
  3. concentrationthe filtrate is concentrated in vacuo
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed successively with water, saturated NaHCO3 solution and water
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. stirringwith stirring into 700 ml of petroleum ether
  9. filtrationThe precipitate is filtered off with suction
  10. customdried

Sources & evidence

ORD record
ord-c893d19a3136476b9740872f37ed6d6b
Source dataset
uspto-grants-1992_02
Patent number
US05091367

Reaction notes

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