Ethylene Glycol → HCID 58554741, compound

HRID 449766Notes

Reaction equation

HRID 449766 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[C@@H:10]([N:16]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:22]2[C:17]1=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:11][CH2:12][C:13]([OH:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH2:45](O)[CH2:46][OH:47]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CO.C(Cl)Cl>[CH:27]1[C:28]2[N:16]([C@@H:10]([CH2:11][CH2:12][C:13]([O:15][CH2:45][CH2:46][OH:47])=[O:14])[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:29])[C:17]3[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]=2[CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 174Ethylene GlycolHCID 10868DicyclohexylcarbodiimideHCID 58554743HCID 58554743, compound

Product 1

HCID 58554741HCID 58554741, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 22 (1.2 g, 3.10 mmol) in CH2Cl2 (20 mL) were added DCC (0.703 g, 3.40 mmol) and catalytic amount of DMAP (0.057 g, 0.46 mmol) under nitrogen atmosphere. The reaction mixture was cooled to 0° C. and ethylene glycol (0.770 g, 0.680 mL, 12.4 mmol) in CH2Cl2 (5 mL) was added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 12 h. The solid DCU was removed by filtration and the filtrate was evaporated under reduced pressure. The crude residue obtained was dissolved in CH2Cl2 (100 mL), washed with water (40 mL×2), brine (40 mL×2), dried over Na2SO4, filtrated and then concentrated to get a yellow residue. A flash chromatography using CH3OH:CH2Cl2 (1:99) as eluent afforded (S)-1-benzyl 5-(2-hydroxyethyl) 2-(9H-carbazol-9-yl)pentanedioate 23 (0.950 g, 71%) as a yellow gummy liquid.

Workup

  1. temperatureto warm up to room temperature
  2. customThe solid DCU was removed by filtration
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe crude residue obtained
  5. washwashed with water (40 mL×2), brine (40 mL×2)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltrated
  8. concentrationconcentrated
  9. customto get a yellow residue

Sources & evidence

ORD record
ord-173590a85a1f44b086e6469440d90ea3
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Reaction notes

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