(Diethylamino)sulfur trifluoride → HCID 90060353, compound

HRID 1779222Notes

Reaction equation

HRID 1779222 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]2([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[O:46][CH2:45][CH2:44][O:43]2)[C@@:22]([OH:33])([CH2:30][CH2:31]O)[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].C(N(S(F)(F)[F:60])CC)C>O1CCCC1>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([NH:18][C:19]([C@@H:21](/[CH:34]=[CH:35]/[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42]2([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[O:46][CH2:45][CH2:44][O:43]2)[C@:22]([CH2:30][CH2:31][F:60])([OH:33])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:20])[C:14]([O:16][CH3:17])=[O:15])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 118260167HCID 118260167, compound

Product 1

HCID 90060353HCID 90060353, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-2-(2-hydroxy-ethyl)-undec-4-enoate (157 mg, 0.211 mmol) was dissolved in tetrahydrofuran (5.0 mL), and (diethylamino)sulfur trifluoride (0.0360 mL, 0.273 mmol) was then added at room temperature. The mixture was stirred for 4 hours, then quenched with a saturated aqueous solution (15 mL) of sodium bicarbonate, and extracted with dichloromethane (15 mL). The organic layer was then dried over anhydrous sodium sulfate and filtered. The solvent was distilled off under reduced pressure. The residue was purified on Biotage (silica gel, n-hexane/ethyl acetate) to obtain 71.1 mg (0.0953 mmol, 45% yield) of tert-butyl (E)-(2S,3S)-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonyl-ethylcarbamoyl]-2-(2-fluoro-ethyl)-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-undec-4-enoate.

Workup

  1. customquenched with a saturated aqueous solution (15 mL) of sodium bicarbonate
  2. extractionextracted with dichloromethane (15 mL)
  3. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified on Biotage (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c58f5d5407e54593b9a9f7e0e6aea6c8
Source dataset
uspto-grants-2016_02
Patent number
US09266853B2

Reaction notes

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