Acetic Anhydride → N-[2-(tert-Butoxycarbonylmethylamino)ethyl]-N-methylacetamide

HRID 17494Notes

Reaction equation

HRID 17494 reaction equation
C(OC(=O)C)(=[O:3])C.[CH2:8]([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])C.[C:15]([O:19][C:20]([CH2:22][NH:23]CCNC)=[O:21])([CH3:18])([CH3:17])[CH3:16]>ClCCl>[C:15]([O:19][C:20]([CH2:22][NH:23][CH2:12][CH2:11][N:10]([CH3:8])[C:13](=[O:3])[CH3:14])=[O:21])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 59921864HCID 59921864, compound

Product 1

HCID 86630858N-[2-(tert-Butoxycarbonylmethylamino)ethyl]-N-methylacetamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen atmosphere, acetic anhydride (1.16 ml, 12.3 mmol) and triethylamine (2.28 ml, 16.4 mmol) were added to a dichloromethane (41 ml) solution of [2-(tert-butoxycarbonylmethylamino)ethyl]methylamine (I-202) (1.54 g, 8.18 mmol) with cooling with ice, followed by stirring at room temperature for 15 hours. The solvent was evaporated away under reduced pressure, then the resulting residue was subjected to silica gel column chromatography, and the eluate with dichloromethane/methanol (10:1, v/v) gave the entitled compound (1.88 g, 100%) as a colorless oil.

Workup

  1. temperaturewith cooling with ice
  2. customThe solvent was evaporated away under reduced pressure

Sources & evidence

ORD record
ord-422600918c5448baa5b1af786fee5d8d
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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