Glycerol → HCID 23387485, compound

HRID 989992Notes

Reaction equation

HRID 989992 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>CN(C)C1C=CN=CC=1.CCOC(C)=O.CCCCCC>[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

6

Reactant 3

HCID 753GlycerolHCID 10868DicyclohexylcarbodiimideHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 23387485HCID 23387485, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 21226206Ethyl acetate hexaneSolvent

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 CH2C2-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-4a0c6ea3be6e4c318be47992ed81e1b4
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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