Tetrahydrofuran → HCID 67269702, compound

HRID 1039704Notes

Reaction equation

HRID 1039704 reaction equation
[Si:1]([O:8][CH:9]([CH2:27][O:28][Si](C(C)(C)C)(C)C)[CH:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C@H:11]([F:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1COCC1>N1C=CC=CC=1>[Si:1]([O:8][CH:9]([CH2:27][OH:28])[CH:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C@H:11]([F:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 67270665HCID 67270665, compound

Product 1

HCID 67269702HCID 67269702, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a plastic bottle containing (R)-tert-butyl 3,4-bis(tert-butyldimethylsilyloxy)-1-fluoro-1-phenylbutan-2-ylcarbamate was added 10 ml THF, 3 ml pyridine, 1 ml HF-pyr at 0° C. The mixture was stirred for 6 h and then carefully quench with sodium bicarbonate. The aq. layer was extracted with DCM (4×25 ml). The combined organics were washed with brine, dried with sodium sulfate, filtered, concentrated and the crude purified on a 40 g ISCO column to give 225 mg of the title compound.

Workup

  1. customcarefully quench with sodium bicarbonate
  2. extractionThe aq. layer was extracted with DCM (4×25 ml)
  3. washThe combined organics were washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe crude purified on a 40 g ISCO column

Sources & evidence

ORD record
ord-e93e20c3987c40c68ccdc0cac4f3e30c
Source dataset
uspto-grants-2013_10
Patent number
US08552181B2

Reaction notes

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