Triethylamine → 5-(tert-Butoxycarbonylaminomethyl)-3-phenylisoxazole

HRID 2111671Notes

Reaction equation

HRID 2111671 reaction equation
Cl[C:2](=[N:9][OH:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:11]([O:15][C:16]([NH:18][CH2:19][C:20]#[CH:21])=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C1COCC1>[C:11]([O:15][C:16]([NH:18][CH2:19][C:20]1[O:10][N:9]=[C:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:21]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756315N-hydroxybenzenecarboximidoyl chlorideHCID 11073648tert-butyl N-(prop-2-yn-1-yl)carbamate

Product 1

HCID 672837925-(tert-Butoxycarbonylaminomethyl)-3-phenylisoxazoleYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of α-chlorobenzaldehyde oxime (Method 22; 1 g, 6.4 mmol) in THF (13 ml) was added dropwise to a solution of N-tert-butoxycarbonyl-propargylamine (0.5 g, 3.2 mmol) and triethylamine (0.9 ml, 6.4 mmol) in THF (25 ml) cooled with an ice bath. The mixture was allowed to warm to ambient temperature and stirred for 2 days. The volatiles were removed by evaporation and the residue dissolved in DCM. The solution was washed with water and brine, dried (MgSO4) and the solvent removed by evaporation. The residue was triturated with isohexane/ether (9:1) and collected by filtration to give the title compound (473 mg, 54%). NMR (CDCl3) 1.45 (s, 9H), 4.45 (d, 2H), 5.10 (bs, 1H), 6.5 (s, 1H), 7.42 (m, 3H), 7.8 (m, 2H).

Workup

  1. temperaturecooled with an ice bath
  2. customThe volatiles were removed by evaporation
  3. dissolutionthe residue dissolved in DCM
  4. washThe solution was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was triturated with isohexane/ether (9:1)
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-b58b1f272343400a9b2fbe052cc1e33a
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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