Tetrabutylammonium Fluoride → ethyl [4-((2R,3R)-3-{[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}-4-oxo-1-phenylazetidin-2-yl)phenoxy]acetate

HRID 254084Notes

Reaction equation

HRID 254084 reaction equation
[NH:1]([C@@H:8]([C:40]1[CH:52]=[CH:51][C:43]([O:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:42][CH:41]=1)[C@@H:9]([S:24][CH2:25][C:26]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:31][CH2:30][C:29]([CH3:33])([CH3:32])[CH2:28][O:27]1)[C:10](=[O:23])N1[C@@H](C2C=CC=CC=2)COC1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C/C(/O[Si](C)(C)C)=N\[Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:33][C:29]1([CH3:32])[CH2:28][O:27][C:26]([CH2:25][S:24][C@H:9]2[C:10](=[O:23])[N:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@@H:8]2[C:40]2[CH:41]=[CH:42][C:43]([O:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[CH:51][CH:52]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:31][CH2:30]1

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 6913588N,O-bis(trimethylsilyl)acetamideHCID 86619085Ethyl (4-{(1S,2R)-1-anilino-2-{[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}-3-oxo-3-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]propyl}phenoxy)acetate

Product 1

HCID 86619084ethyl [4-((2R,3R)-3-{[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}-4-oxo-1-phenylazetidin-2-yl)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl (4-{(1S,2R)-1-anilino-2-{[(5,5-dimethyl-2-phenyl-1,3-dioxan-2-yl)methyl]thio}-3-oxo-3-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]propyl}phenoxy)acetate (2.1 g, 2.9 mmol) was dissolved in dry toluene (200 ml) and heated to 90° C. under inert atmosphere. N,O-Bis(trimethylsilyl)acetamide (BSA, 2.1 ml, 8.7 mmol) was added and the mixture was stirred at 90° C. for one hour. At 45° C. tetrabutylammonium fluoride (TBAF, cat., 0.1 g) was added and the mixture was stirred at 45° C. for 18 h. The mixture was concentrated under reduced pressure. The residue was purified by flash-chromatography (hexane:EtOAc 5:1). This afforded 0.98 g (60%) of the title compound as a yellow oil. 1H-NMR (CDCl3, 200 MHz): 0.6 (s, 3H), 1.2-1.4 (m, 6H), 3.0-3.2 (t, broad, 2H), 3.3-3.5 (m, 4H), 3.95 (d, 1H), 4.2-4.4 (q, 2H), 4.6 (s, 2H), 4.8 (d, 1H), 6.9-7.1 (m, 3H), 7.2-7.6 (m, 1H). MS (CI) M/z: 584.2 (M++Na).

Workup

  1. stirringthe mixture was stirred at 45° C. for 18 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residue was purified by flash-chromatography (hexane:EtOAc 5:1)

Sources & evidence

ORD record
ord-5523f0e7d2f142edb8398895767ca1df
Source dataset
uspto-grants-2011_01
Patent number
US07871998B2

Reaction notes

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