Acetic Acid → Methyl 3-[2-(2-{2-[2-((tert-butoxycarbonyl)(methyl)amino)ethoxy]ethoxy}ethoxy)ethoxy]propanoate

HRID 446653Notes

Reaction equation

HRID 446653 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]([O:12][C:13]([N:15]([CH3:33])[CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:14])([CH3:11])([CH3:10])[CH3:9].C(O)(=O)C>CCCCCC.CO>[C:8]([O:12][C:13]([N:15]([CH3:33])[CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][C:30]([O:32][CH3:1])=[O:31])=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 86671296N-methyl-N-(t-Boc)-PEG4-acid

Product 1

HCID 86671295Methyl 3-[2-(2-{2-[2-((tert-butoxycarbonyl)(methyl)amino)ethoxy]ethoxy}ethoxy)ethoxy]propanoate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

2 ml of a 2M solution of trimethylsilyldiazomethane in hexane are added to a solution, cooled to 0° C., of 500 mg of 3-[2-(2-{2-[2-((tert-butoxycarbonyl)(methyl)amino)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid in 4.8 ml of MeOH. After 2 h, the mixture is neutralized by addition of 120 μl of acetic acid and then concentrated under RP, and the residue is purified by flash chromatography on silica (Analogix Super Flash SiO2 SF25-40 g) using a gradient from 0 to 5% of methanol in DCM. 400 mg of methyl 3-[2-(2-{2-[2-((tert-butoxycarbonyl)(methyl)amino)ethoxy]ethoxy}ethoxy)ethoxy]propanoate are thus obtained.

Workup

  1. concentrationconcentrated under RP
  2. customthe residue is purified by flash chromatography on silica (Analogix Super Flash SiO2 SF25-40 g)

Sources & evidence

ORD record
ord-dafdac3e54cb47a69b579d2a2718814e
Source dataset
uspto-grants-2013_07
Patent number
US08481042B2

Reaction notes

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