Diisopropylethylamine → (S)-6-(2-Hydroxy-2-methyl-propyl)-6-phenyl-3-((S)-1-{4-[1-((S)-tetrahydro-furan-2-carbonyl)-piperidin-4-yl]-phenyl}-ethyl)-[1,3]oxazinan-2-one

HRID 80972Notes

Reaction equation

HRID 80972 reaction equation
F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.[O:23]1[CH2:27][CH2:26][CH2:25][C@H:24]1[C:28]([OH:30])=O.C(N(C(C)C)CC)(C)C.[OH:40][C:41]([CH3:71])([CH3:70])[CH2:42][C@@:43]1([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[O:48][C:47](=[O:49])[N:46]([C@H:50]([C:52]2[CH:57]=[CH:56][C:55]([CH:58]3[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]3)=[CH:54][CH:53]=2)[CH3:51])[CH2:45][CH2:44]1>CN(C)C=O>[OH:40][C:41]([CH3:70])([CH3:71])[CH2:42][C@@:43]1([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[O:48][C:47](=[O:49])[N:46]([C@H:50]([C:52]2[CH:57]=[CH:56][C:55]([CH:58]3[CH2:63][CH2:62][N:61]([C:28]([C@@H:24]4[CH2:25][CH2:26][CH2:27][O:23]4)=[O:30])[CH2:60][CH2:59]3)=[CH:54][CH:53]=2)[CH3:51])[CH2:45][CH2:44]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 446666Tetrahydro-2-furoic acid, (-)-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 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 67503375(S)-6-(2-Hydroxy-2-methyl-propyl)-6-phenyl-3-((S)-1-{4-[1-((S)-tetrahydro-furan-2-carbonyl)-piperidin-4-yl]-phenyl}-ethyl)-[1,3]oxazinan-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (125 mg) was added to a solution of (S)-tetrahydro-furan-2-carboxylic acid (45 mg) and diisopropylethyl-amine (200 μL) in N,N-dimethylformamide (2 mL) at room temperature. The resulting solution was stirred for 30 min, before (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) dissolved in dimethylformamide (1 mL) was added. The resulting solution was stirred at room temperature overnight and then concentrated under reduced pressure. The crude product was purified by HPLC on reversed phase (MeCN/H2O/NH3) to afford the title compound.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by HPLC on reversed phase (MeCN/H2O/NH3)

Sources & evidence

ORD record
ord-6f79aac3852f4320951bba737cd5dab0
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Reaction notes

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