Tetrabutylammonium Fluoride → HCID 58109397, compound

HRID 2037489Notes

Reaction equation

HRID 2037489 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][C@@:12]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:17][C:16](=[O:18])[N:15]([C@H:19]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][O:28][CH3:29])=[CH:23][CH:22]=2)[CH3:20])[CH2:14][CH2:13]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CCOC(C)=O>[OH:8][CH2:9][CH2:10][CH2:11][C@@:12]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[O:17][C:16](=[O:18])[N:15]([C@H:19]([C:21]2[CH:22]=[CH:23][C:24]([CH2:27][O:28][CH3:29])=[CH:25][CH:26]=2)[CH3:20])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58109721HCID 58109721, compound

Product 1

HCID 58109397HCID 58109397, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-6-(3-(tert-butyldimethylsilyloxy)propyl)-3-((S)-1-(4-(methoxymethyl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (7 mg, 0.02 mmol) in EtOAc (5 mL) was added TBAF (26.1 mg, 0.10 mmol) at rt, and the mixture was stirred at rt overnight. The mixture was concentrated in vacuo to give the crude product, which was purified by preparative TLC followed by preparative HPLC to afford (R)-6-(3-hydroxypropyl)-3-((S)-1-(4-(methoxymethyl)phenyl)ethyl)-6-phenyl-1,3-oxazinan-2-one (1.63 mg). LC-MS Method 3 tR=0.96, min, m/z=406; 1H NMR (CDCl3): 1.39 (m, 1H), 1.49 (m, 3H), 1.71 (m, 1H), 1.89 (m, 3H), 2.01 (m, 1H), 2.18 (m, 2H), 2.75-2.88 (m, 3H), 3.23 (m, 1H), 3.48 (m, 1H), 3.70 (m, 1H) □4.19 (m, 1H), 5.58 (m, 1H), 6.73-6.86 (m, 2H), 7.08-7.29 (m, 6H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give the crude product, which
  3. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-2926d73f26d34a1faad606f23b4b79b3
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…