Triethylamine → HCID 45101411, compound

HRID 80971Notes

Reaction equation

HRID 80971 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][C:7]([CH3:37])([CH3:36])[CH2:8][C@@:9]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:14][C:13](=[O:15])[N:12]([C@H:16]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH3:17])[CH2:11][CH2:10]1.C(N(CC)CC)C>ClCCl>[OH:6][C:7]([CH3:36])([CH3:37])[CH2:8][C@@:9]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:14][C:13](=[O:15])[N:12]([C@H:16]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]3[CH2:29][CH2:28][N:27]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH3:17])[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58109308(S)-6-(2-Hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-piperidin-4-yl-phenyl)-ethyl]-[1,3]oxazinan-2-one

Product 1

HCID 45101411HCID 45101411, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

MeSO2Cl (29 μL) was added to a solution of (S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-piperidin-4-yl-phenyl)-ethyl]-[1,3]oxazinan-2-one (150 mg) and triethylamine (100 μL) in dichloromethane (3 mL) at room temperature. After stirring the solution at room temperature overnight, more dichloromethane was added and the resulting solution was washed with aqueous NaHCO3 solution, water, and brine. The organic solution was then dried (MgSO4) and concentrated. The residue was purified by HPLC on reversed phase (MeCN/H2O/NH3) to afford the title compound.

Workup

  1. additionwas added
  2. washthe resulting solution was washed with aqueous NaHCO3 solution, water, and brine
  3. dry with materialThe organic solution was then dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC on reversed phase (MeCN/H2O/NH3)

Sources & evidence

ORD record
ord-87ddad08e8d84785bad515d8cfe67a89
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Reaction notes

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