Triethylamine → HCID 140555601, compound

HRID 1909113Notes

Reaction equation

HRID 1909113 reaction equation
[C:1]([C@H:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4])#[N:2].Cl.[NH2:17][OH:18].C(N(CC)CC)C>C(O)C>[NH2:2]/[C:1](=[N:17]\[OH:18])/[C@H:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 10703364(R)-benzyl 1-cyanoethylcarbamate

Product 1

HCID 140555601HCID 140555601, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of benzyl [(1R)-1-cyanoethyl]carbamate (2.52 g, 12.3 mmol) in ethanol (30 ml) was added hydroxylamine hydrochloride salt (0.90 g, 13.0 mmol) and triethylamine (3.43 ml, 24.6 mmol) and the mixture heated to 75° C. After 16 h, the solution was concentrated and the residue was dissolved in 200 mL of dichloromethane. The mixture was washed with 100 mL of saturated aqueous sodium bicarbonate (2×) and brine (100 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to give benzyl [(1R,2Z)-2-amino-2-(hydroxyimino)-1-methylethyl]carbamate (2.9 g). MS 238.2 (M+1).

Workup

  1. concentrationthe solution was concentrated
  2. dissolutionthe residue was dissolved in 200 mL of dichloromethane
  3. washThe mixture was washed with 100 mL of saturated aqueous sodium bicarbonate (2×) and brine (100 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f9d8ca1838134210a5efb46b02f08d2a
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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