Acetic Anhydride → HCID 58674936, compound

HRID 2244414Notes

Reaction equation

HRID 2244414 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][OH:15])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[C:33](OC(=O)C)(=[O:35])[CH3:34]>ClCCl>[C:1]([O:5][C:6]([NH:7][C:8]1[N:9]=[C:10]([CH2:14][O:15][C:33](=[O:35])[CH3:34])[CH:11]=[CH:12][CH:13]=1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 19349090Tert-butyl (6-(hydroxymethyl)pyridin-2-yl)carbamate

Product 1

HCID 58674936HCID 58674936, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(6-Hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (0.85 g, 3.79 mmol) was dissolved in dichloromethane (30.00 ml) and triethylamine (1.32 ml) and treated with dimethylaminopyridine (0.09 g, 0.76 mmol) and acetic anhydride (0.43 g, 4.17 mmol). The mixture was stirred at room temperature for 10 min, then partitioned between water and dichloromethane. The organic layer was dried over sodium sulphate and evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate) to yield acetic acid 6-tert-butoxycarbonylamino-pyridin-2-ylmethyl ester (0.85 g, 84%) as a white solid, MS (ISP): m/e=267.1 (M+H+).

Workup

  1. custompartitioned between water and dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customevaporated
  4. customThe residue was purified by flash chromatography (heptane/ethyl acetate)

Sources & evidence

ORD record
ord-966f3bd02db6414a98f8bdebc1893507
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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