1,2-Dichloroethane → HCID 86594383, compound

HRID 902924Notes

Reaction equation

HRID 902924 reaction equation
Cl.[C:2]([O:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].C(N(C(C)C)CC)(C)C.[C:17]([O:21][C:22](=[O:33])[CH2:23][CH:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:25](O)=[O:26])([CH3:20])([CH3:19])[CH3:18].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C1COCC1>[CH2:31]([O:30][C:28](=[O:29])[CH:24]([C:25](=[O:26])[NH:7][O:6][C:2]([CH3:5])([CH3:4])[CH3:3])[CH2:23][C:22]([O:21][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:33])[CH3:32]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 85967320HCID 85967320, compound

Product 1

HCID 86594383HCID 86594383, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring solution of O-tert-butyl hydroxylamine hydrochloride (3.67 g, 29.3 mmol) in dry THF (30 mL) at room temperature was added diisopropylethyl amine (3.60 g, 27.9 mmol). To the resulting mixture was transferred the compound of example 58 (6.87 g, 27.9 mmol), as a solution in dry THF (30 mL), followed by HOBt (5.35 g, 27.9 mmol). The mixture was cooled to 0° C. and EDC (5.35 g, 27.9 mmol) was added in one portion. The reaction mixture was then allowed to warm to room temperature and was stirred for 24 h. The solvent was evaporated and the residue was taken-up into 500 ml of ethyl acetate and subsequently washed with a 5% aqueous solution of KHSO4 (2×200 mL), with a 5% aqueous solution of NaHCO3 (2×200 mL), and finally with water. After drying (anhydrous MgSO4) and evaporation, the crude product was purified by flash chromatography (SiO2, 60% hexane-40% ethyl acetate) to afford 5.93 g (66.0% yield) of the desired product: 1H NMR (CDCl3, 400 MHz) 8.61 (s, 1H), 4.20 (q, 2H), 3.55 (t, 1H), 2.93 (d, 3H), 1.43 (s, 9H), 1.28 (s, 9H); 13C NMR (CDCl3, 400 MHz) 195.8, 171.2, 169.7, 83.1, 81.9, 62.4, 46.8, 34.1, 28.4, 26.6, 14.5.

Workup

  1. temperatureto warm to room temperature
  2. customThe solvent was evaporated
  3. washsubsequently washed with a 5% aqueous solution of KHSO4 (2×200 mL), with a 5% aqueous solution of NaHCO3 (2×200 mL)
  4. customAfter drying
  5. custom(anhydrous MgSO4) and evaporation
  6. customthe crude product was purified by flash chromatography (SiO2, 60% hexane-40% ethyl acetate)

Sources & evidence

ORD record
ord-bdfa645c27554d768556c1c647a29e2c
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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