Acetic Acid → HCID 23387515, compound

HRID 489046Notes

Reaction equation

HRID 489046 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][C:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][OH:22])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Na+].C(O)(=[O:31])C>CC(C)=O>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][C:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[C:21]([OH:31])=[O:22])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5234Sodium ChlorideHCID 53986985HCID 53986985, compound

Product 1

HCID 23387515HCID 23387515, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a cooled mixture of chromic anhydride (8.5 g, 85,2 mmole) in 100 ml acetic acid was added dropwise a solution of 2-(N-benzyloxycarbonyl-L-valyloxymethyl)-2-ethyl-butan-1-ol (10.4 g, 28.4 mmole) in 50 ml acetone and the mixture was stirred 24 hours at room temperature. The mixture was added to 1000 ml 10% sodium chloride solution and extracted four times with ethyl acetate. The organic phase was washed twice with brine, dried with sodium sulfate and evaporated under reduced pressure. The product was isolated by silica gel column chromatography with hexane/ethyl acetate. Yield: 7 g=65%. The product can be activated and esterified directly to a drug or further modified as described below.

Workup

  1. extractionextracted four times with ethyl acetate
  2. washThe organic phase was washed twice with brine
  3. dry with materialdried with sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe product was isolated by silica gel column chromatography with hexane/ethyl acetate

Sources & evidence

ORD record
ord-73438f7e4ed54ba8bda1126cd24b5d6a
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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