Dicyclohexylcarbodiimide → HCID 21848657, compound

HRID 618812Notes

Reaction equation

HRID 618812 reaction equation
[CH3:1][S:2]([N:5]([CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH3:23])[CH:21]=2)[O:16][C:15]([CH3:25])([CH3:24])[CH2:14]1)[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])(=[O:4])=[O:3].[CH2:26](N(CCO)C)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1CC[CH:41]([N:44]=[C:45]=NC2CCCCC2)[CH2:40]C1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][S:2]([N:5]([CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH3:23])[CH:21]=2)[O:16][C:15]([CH3:25])([CH3:24])[CH2:14]1)[CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:40][CH2:41][NH:44][CH2:45][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:11])(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 66876N-Benzyl-N-methylethanolamineHCID 21848627HCID 21848627, compound

Product 1

HCID 21848657HCID 21848657, compoundYield 64.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.5 g (1.35 mmol) of 5-[methylsulfonyl-(2,2,6-trimethylchroman-4-yl)amino]pentanoic acid, 0.25 g (1.5 mmol) of 2-(N-benzyl-N-methylamino)ethanol, 0.31 g (1.5 mmol) of DCC and a spatula tipful of DMAP in 10 ml of methylene chloride is stirred overnight at RT. After filtering off the precipitate, the solution is concentrated and the crude product is purified by chromatography on silica gel using methylene chloride/methanol 97:3, and 0.45 g of 2-(benzylmethylamino)ethyl 5-[methanesulfonyl-(2,2,6-trimethylchroman-4-yl)amino]pentanoate is obtained.

Workup

  1. filtrationAfter filtering off the precipitate
  2. concentrationthe solution is concentrated
  3. customthe crude product is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8e8c21670cdf4937b73581443d377fa8
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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