Dicyclohexylcarbodiimide → HCID 18655967, compound

HRID 2379011Notes

Reaction equation

HRID 2379011 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH2:12][C@H:13]([CH:15]([CH3:17])[CH3:16])[N:14]=2)=[CH:6][CH:5]=1)([OH:3])=[O:2].[C:18]([O:23][CH3:24])(=[O:22])[C@H:19]([CH3:21])O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:24][O:23][C:18]([C@@H:19]([O:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][CH2:12][C@H:13]([CH:15]([CH3:17])[CH3:16])[N:14]=2)=[CH:6][CH:5]=1)=[O:3])[CH3:21])=[O:22]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 94386methyl (S)-lactateHCID 54319561HCID 54319561, compound

Product 1

HCID 18655967HCID 18655967, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(S)-2-(4-Carboxyphenyl)-4-isopropyl-2-oxazoline (2.0 g), 0.5 g of methyl (S)-lactate and 0.1 g of 4-(dimethylamino)pyridine are dissolved in 50 ml of dichloromethane and the solution is treated portionwise with 1.4 g of N,N'-dicyclohexylcarbodiimide within 10 minutes while stirring. The mixture is stirred at room temperature overnight and then filtered. The filtrate is diluted with dichloromethane, washed twice with 50 ml of saturated sodium carbonate solution each time and then with water, dried over magnesium sulphate and concentrated. The crude product obtained is purified by chromatography on silica gel with toluene. The (S)-2-[4-([(S)-1-(methoxycarbonyl)-1-ethoxy]carbonyl)phenyl]-4-isopropyl-2-oxazoline obtained is recrystallized from ethanol;

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. filtrationfiltered
  3. additionThe filtrate is diluted with dichloromethane
  4. washwashed twice with 50 ml of saturated sodium carbonate solution each time
  5. dry with materialwith water, dried over magnesium sulphate
  6. concentrationconcentrated
  7. customThe crude product obtained
  8. customis purified by chromatography on silica gel with toluene

Sources & evidence

ORD record
ord-8fe21eb3624b4bee864287fb81df9277
Source dataset
uspto-grants-1994_11
Patent number
US05360577

Reaction notes

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