Triethylamine → HCID 58109139, compound

HRID 2037512Notes

Reaction equation

HRID 2037512 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)([CH2:16][CH2:17][OH:18])[O:12][C:11]2=[O:26])[CH3:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Si:34](Cl)([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:16][CH2:17][O:18][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])([C:19]3[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=3)[O:12][C:11]2=[O:26])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 58109626HCID 58109626, compound

Product 1

HCID 58109139HCID 58109139, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (0.4300 g, 1.02 mmol), 4-dimethylaminopyridine (0.0783 g, 0.64 mmol), triethylamine (0.8 mL, 5.74 mmol), and tert-butyldimethylsilyl chloride (0.2870 g, 1.90 mmol) in CH2Cl2 was stirred for 16 h at rt. After the solvents were removed in vacuo, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to give 0.2856 g of (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-(tert-butyldimethylsilyloxy)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one as a solid. LC-MS Method 1 tR=2.49 min, m/z 560, 558 (MNa+), 538, 536 (MH+), 494, 492; 1H NMR (400 MHz, CDCl3) δ 7.34-7.25 (m, 4H), 7.10-7.05 (m, 2H), 6.78 (d, J=8.5 Hz, 2H), 5.63 (q, J=7.0 Hz, 1H), 3.84-3.78 (m, 1H), 3.44-3.38 (m, 1H), 2.96-2.90 (m, 1H), 2.78-2.27 (m, 3H), 2.18-2.04 (m, 2H), 1.52 (d, J=7.3 Hz, 3H), 0.87 (s, 9H), 0.02 (s, 3H), 0.00 (s, 3H); 19F NMR (376 MHz, CDCl3) δ −114.99 (m).

Workup

  1. customAfter the solvents were removed in vacuo
  2. customthe residue was purified by chromatography on silica gel
  3. washeluted with hexanes/EtOAc

Sources & evidence

ORD record
ord-72df101469104718aaf2d0fd3c6584e0
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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