Sodium Azide → HCID 58109650, compound

HRID 2037571Notes

Reaction equation

HRID 2037571 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C@@:9]1([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[O:14][C:13](=[O:15])[N:12]([C@H:16]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:17])[CH2:11][CH2:10]1)(=O)=O.[N-:31]=[N+:32]=[N-:33].[Na+]>CN(C=O)C>[N:31]([CH2:6][CH2:7][CH2:8][C@@:9]1([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[O:14][C:13](=[O:15])[N:12]([C@H:16]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH3:17])[CH2:11][CH2:10]1)=[N+:32]=[N-:33]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 58109609HCID 58109609, compound

Product 1

HCID 58109650HCID 58109650, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-((R)-3-((S)-1-cyclohexylethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)propyl methanesulfonate (240 mg, 0.54 mmol) in DMF (10 mL) was added NaN3 (112 mg, 1.72 mmol). After stirring at 100° C. for 3 h, the reaction was quenched by H2O, and the mixture was extracted with EtOAc. The organic phase was washed with brine and concentrated to give (R)-6-(3-azidopropyl)-3-((S)-1-cyclohexylethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (180 mg, 88%). 1H NMR (CDCl3): δ=1.04 (m, 6H), 1.21 (m, 1H), 1.41 (m, 1H), 1.5 (m, 2H), 1.7 (m, 1H), 1.8 (m, 7H), 2.12 (m, 1H), 2.3 (m, 1H), 2.6 (m, 1H), 3.01 (m, 2H), 3.22 (m, 2H), 3.92 (m, 1H), 7.02 (m, 2H), 7.3 (m, 2H).

Workup

  1. customthe reaction was quenched by H2O
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic phase was washed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7f4412402ec94297bcead9bfc7c2ffa1
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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