Methylamine → HCID 58109713, compound

HRID 2037452Notes

Reaction equation

HRID 2037452 reaction equation
[CH3:1][NH2:2].[C:3](=O)([O:37]C1C=CC([N+]([O-])=O)=CC=1)[O:4][CH2:5][CH2:6][C@@:7]1([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[O:12][C:11](=[O:13])[N:10]([C@H:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=3[F:29])=[CH:18][CH:17]=2)[CH3:15])[CH2:9][CH2:8]1>C1COCC1>[CH3:1][NH:2][C:3](=[O:37])[O:4][CH2:5][CH2:6][C@@:7]1([C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)[O:12][C:11](=[O:13])[N:10]([C@H:14]([C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=3[F:29])=[CH:20][CH:21]=2)[CH3:15])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 66856160HCID 66856160, compound

Product 1

HCID 58109713HCID 58109713, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylamine (15 mg, 0.22 mmol) and TEA (2 mL) was added to a solution of 2-((S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl 4-nitrophenyl carbonate (70 mg, crude) in 8 mL of THF. The mixture was stirred at rt overnight. The reaction was quenched with saturated NH4Cl. The mixture was extracted with EtOAc for 3 times, washed with brine, dried over anhydrous Na2SO4 and concentrated to give the residue, which was purified by preparative HPLC to give 2-((S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl methylcarbamate (5 mg, 9%). 1H NMR (CDCl3): 1.55 (m, 3H), 2.36 (m, 5H), 2.74 (m, 3H), 2.99 (m, 1H), 4.09 (m, 2H), 5.71 (m, 1H), 6.92 (m, 2H), 7.04 (m, 4H), 7.33 (m, 5H). LC-MS Method 3 tR=1.32 min, m/z=513, 535.

Workup

  1. customThe reaction was quenched with saturated NH4Cl
  2. extractionThe mixture was extracted with EtOAc for 3 times
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto give the residue, which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-27f8e0eb6d1146d2ab9e46127f28ca50
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…