Acetic Acid → N-methyl-N-(t-Boc)-PEG4-acid

HRID 446654ノート

反応式

HRID 446654 の反応式
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:9])([CH3:6])([CH3:5])[CH3:4].IC.[C:30](O)(=O)C>C1COCC1>[C:3]([O:7][C:8]([N:10]([CH3:30])[CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:9])([CH3:6])([CH3:4])[CH3:5]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 6328Methyl iodide3 回HCID 24758Sodium hydride2 回HCID 27560011-(((Tert-butoxy)carbonyl)amino)-3,6,9,12-tetraoxapentadecan-15-oic acid

生成物 1

HCID 86671296N-methyl-N-(t-Boc)-PEG4-acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

85.4 mg of NaH are added portionwise to a solution, cooled to 0° C., of 520 mg of 3-[2-(2-{2-[2-((tert-butoxycarbonyl)amino)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid in 14 ml of THF. After stirring for 5 min, 150 μl of iodomethane are added. The mixture is then stirred at AT for 2 h and then an additional 150 μl of iodomethane are added. After 12 h at AT, the mixture is hydrolysed and then brought to acidic pH by addition of aqueous acetic acid at 0° C. The aqueous phase is extracted 3× with AcOEt, the combined organic phases are dried over MgSO4 and concentrated under RP, and the crude product obtained is reacted again according to the same protocol with 85 mg of NaH and 176 μl of iodomethane for an additional 2 h. 500 mg of 3-[2-(2-{2-[2-((tert-butoxycarbonyl)(methyl)amino)ethoxy]ethoxy}ethoxy)ethoxy]propanoic acid are thus obtained.

後処理

  1. stirringThe mixture is then stirred at AT for 2 h
  2. waitAfter 12 h at AT
  3. extractionThe aqueous phase is extracted 3× with AcOEt
  4. dry with materialthe combined organic phases are dried over MgSO4
  5. concentrationconcentrated under RP
  6. customthe crude product obtained
  7. customis reacted again

出典と根拠

ORDレコード
ord-cd53b5a9991f4787a05fbfb75bda106a
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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