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

HRID 446653ノート

反応式

HRID 446653 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8058Hexane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-dafdac3e54cb47a69b579d2a2718814e
出典データセット
uspto-grants-2013_07
特許番号
US08481042B2

反応ノート

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