Triethylamine → HCID 86615676, compound

HRID 2261905Notes

Reaction equation

HRID 2261905 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:19])([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:10]=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:21][OH:22].C(N(CC)CC)C>C(O)C>[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:19])([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:10]=[N:21][OH:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 443297Hydroxyamine hydrochloride2×HCID 58990158HCID 58990158, compound

Product 1

HCID 86615676HCID 86615676, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (R)-2-tert-butoxycarbonylamino-2-methyl-3-phenylpropanal (80 mg, 0.30 mmol), hydroxylamine hydrochloride (25 mg, 0.36 mmol) and triethylamine (0.125 mL, 0.9 mmol) in 3.4 mL ethanol was heated to reflux temperature overnight. Additional hydroxylamine hydrochloride (25 mg, 0.36 mmol) and triethylamine (0.125 mL, 0.9 mmol) were added and the reaction continued at reflux temperature for 4.5 h. Concentration and flash chromatography (0-25% EtOAc/hexanes) gave (R)-2-tert-butoxycarbonylamino-2-methyl-3-phenylpropanal oxime. 1H NMR (CDCl3) δ 7.95 (bs, 1H), 7.52 (bs, 1H), 7.25 (m, 3H), 7.10 (d, J=6.7 Hz, 2H), 5.01 (s, 1H), 3.14 (m, 2H), 1.46 (s, 9H), 1.42 (s, 3H).

Workup

  1. temperatureto reflux temperature overnight
  2. temperatureat reflux temperature for 4.5 h
  3. concentrationConcentration and flash chromatography (0-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d8fb19cf67624f16a718fb51b9ae604c
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

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