Glycerol → HCID 23387485, compound

HRID 1170648Notes

Reaction equation

HRID 1170648 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[OH:19][CH2:20][CH:21]([CH2:23]O)[OH:22].C1(N=C=NC2CCCCC2)CCCCC1.CCOC(C)=O.CCCCCC>CN(C)C1C=CN=CC=1.C(Cl)Cl.CO>[C:1]([NH:11][C@H:12]([C:16]([O:18][CH2:23][CH:21]([CH2:20][OH:19])[OH:22])=[O:17])[CH:13]([CH3:14])[CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

7

Reactant 4

HCID 753GlycerolHCID 10868DicyclohexylcarbodiimideHCID 726987N-Carbobenzoxy-L-valineHCID 21226206Ethyl acetate hexane

Product 1

HCID 23387485HCID 23387485, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

CBz-L-valine (4.35 g, 17.3 mmol) was added to a fivefold excess of glycerol (8 ml, 86.9 mmol) together with dicyclohexylcarbodiimide (4.29 g 20.8 mmol) and 4-dimethylaminopyridine (0.212 g) at room temperature. After stirring overnight the suspension was filtered and DMF removed in vacuo from the filtrate. The residue was redissolved in CH2Cl2, washed successively with saturated NaHCO3, brine, and water and then dried. The crude material was chromatographed on silica gel with 4/1 EtOAc-hexane as eluent to yield 2.465 g. Rf (4/1 EtOAc-hexane) 0.17, (20/1 CH2Cl2-methanol) 0.12.

Workup

  1. filtrationwas filtered
  2. customDMF removed in vacuo from the filtrate
  3. dissolutionThe residue was redissolved in CH2Cl2
  4. washwashed successively with saturated NaHCO3, brine, and water
  5. customdried
  6. customThe crude material was chromatographed on silica gel with 4/1 EtOAc-hexane as eluent
  7. customto yield 2.465 g

Sources & evidence

ORD record
ord-b08931dcb44e4784b581fb6e603d831d
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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