Pyridine → tert-butyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3-fluorophenyl)-4-oxobutan-2-ylcarbamate

HRID 20008Notes

Reaction equation

[Si:1]([O:8][C@H:9]([CH2:27][OH:28])[C@@H:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(Cl)Cl.N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>CCOC(C)=O>[Si:1]([O:8][C@H:9]([CH:27]=[O:28])[C@@H:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 23 °C

Procedure

To a 150 mL RBF containing tert-butyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(3-fluorophenyl)-4-hydroxybutan-2-ylcarbamate (170.00 mg, 411 μmol) was added DCM (10 mL) and the mixture was allowed to stir at 23° C. for 2 minutes. At this time, pyridine (299 μl, 3699 μmol) was added via syringe before the addition of Dess-MartinPeriodinane (262 mg, 617 μmol) in one portion. The reaction stayed a clear solution and was allowed to stir 1 h before loading directly to a silica gel column (20% EtOAc). The purified product was concentrated to give the title compound as a colorless oil.

Workup

concentrationThe purified product was concentrated

Sources & evidence

ORD record: ord-e5daab64725749169af83e097ae14fc0
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745484B2

Reaction notes

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