Ammonium Chloride → Tert-Butyl (2S,3R)-3-(tert-butyldimethylsilyloxy)-1-phenylpent-4-en-2-ylcarbamate

HRID 253141Notes

Reaction equation

[OH:1][C@H:2]([CH:19]=[CH2:20])[C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O([Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])S(C(F)(F)F)(=O)=O.[Cl-].[NH4+]>C(Cl)Cl>[Si:29]([O:1][C@H:2]([CH:19]=[CH2:20])[C@@H:3]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30]

Participants

Conditions

Temperature: 23 °C

Procedure

To a 250 mL round bottom flask containing tert-butyl (2S,3R)-3-hydroxy-1-phenylpent-4-en-2-ylcarbamate (3.080 g, 11 mmol) was added DCM (50 mL) and the mixture was allowed to stir at 23° C. for 2 min. At this time, TEA (4.7 ml, 33 mmol) was added via syringe before dropwise addition of tert-butyldimethylsilyl triflate (2.8 ml, 12 mmol). The reaction was allowed to stir for 4 h and then poured into saturated ammonium chloride. The aqueous layer was extracted with DCM (3×75 mL) and the combined organics were washed with brine and dried with sodium sulfate. The solution was filtered and concentrated to provide 4.47 g of a yellow solid. The material was taken on to the next step without any further purification.

Workup

stirringto stir for 4 h
extractionThe aqueous layer was extracted with DCM (3×75 mL)
washthe combined organics were washed with brine
dry with materialdried with sodium sulfate
filtrationThe solution was filtered
concentrationconcentrated

Sources & evidence

ORD record: ord-346f32a77b134b81b8a28bf0be8f17c8
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872009B2

Reaction notes

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