Dicyclohexylcarbodiimide → HCID 15859752, compound

HRID 618808Notes

Reaction equation

HRID 618808 reaction equation
[CH2:1]([S:3]([N:6]([CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH3:24])[CH:22]=2)[O:17][C:16]([CH3:26])([CH3:25])[CH2:15]1)[CH2:7][CH2:8][CH2:9][CH2:10][C:11](O)=[O:12])(=[O:5])=[O:4])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH2:52]([N:54]([CH2:57][CH2:58][NH2:59])[CH2:55][CH3:56])[CH3:53]>CN(C=O)C.CC(=O)OCC.O>[CH2:52]([N:54]([CH2:55][CH3:56])[CH2:57][CH2:58][NH:59][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][N:6]([S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([CH3:24])[CH:22]=2)[O:17][C:16]([CH3:26])([CH3:25])[CH2:15]1)[CH3:53]

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 60993N,N-DiethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 21848652HCID 21848652, compound

Product 1

HCID 15859752HCID 15859752, compoundYield 79.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.3 g (0.78 mmol) of 5-[ethylsulfonyl-(2,2,6-trimethylchroman-4-yl)amino]pentanoic acid, 0.11 g (0.78 mmol) of HOBT and 0.18 g (0.86 mmol) of DCC in 4 ml of DMF is stirred at 0° C. for 1 h. 0.09 g (0.78 mmol) of diethylaminoethylamine is then added and the mixture is stirred overnight at RT. It is treated with 50 ml of water and 50 ml of EA, and the organic phase is washed twice with 25 ml each of saturated sodium bicarbonate solution and additionally twice with water. After drying over magnesium sulfate and concentrating in vacuo, 0.3 g of 5-[ethylsulfonyl-(2,2,6-trimethylchroman-4-yl)amino]pentanoic acid (2-diethylaminoethyl)amide is obtained.

Workup

  1. washthe organic phase is washed twice with 25 ml each of saturated sodium bicarbonate solution and additionally twice with water
  2. dry with materialAfter drying over magnesium sulfate
  3. concentrationconcentrating in vacuo

Sources & evidence

ORD record
ord-fd8a5b91d31d4d3eb4ac97033ff9e015
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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