Sodium Iodide → Succinic acid benzyl ester iodomethyl ester

HRID 989930Notes

Reaction equation

HRID 989930 reaction equation
Cl[CH2:2][O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].[I-:18].[Na+]>C(#N)C>[I:18][CH2:2][O:3][C:4](=[O:17])[CH2:5][CH2:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 10801108Butanedioic acid, chloromethyl phenylmethyl ester

Product 1

HCID 54300300Succinic acid benzyl ester iodomethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Benzyloxycarbonylpropionic acid chloromethyl ester (2 g, 1.38 mmole) was dissolved in acetonitrile (30 ml). Sodium iodide (1.6 g, 10.9 mmole) was added to the solution After reaction at 70° C. for 3 hr, the reaction mixture was filtered and the residue was dissolved in methylene chloride (20 ml) and refiltered. The solution was dried and gave internediate 3-benzyloxycarbonylpropionic acid iodomethyl ester in quantitative yield. This intermediate is bonded to an accessible function of a drag, such as a ring hydroxy or carboxy function using conventional alkylation/acylation conditions as described generally herein. Following deprotection of the terminal carboxy, a di/trifunctional linker bearing R2, such as 1,3-bis-O-(L-valyl)glycerol or iodomethyloxy-L-valyl is acylated/alkylated thereon or R2 amide bonded thereon by conventional techniques as described herein, such as with DCC coupling agent.

Workup

  1. customAfter reaction at 70° C. for 3 hr
  2. filtrationthe reaction mixture was filtered
  3. dissolutionthe residue was dissolved in methylene chloride (20 ml)
  4. customThe solution was dried

Sources & evidence

ORD record
ord-e3287b133501432385202367a8425a6b
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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