Potassium Carbonate → 5-tert-Butoxycarbonylamino-3-(3-fluoro-4-nitro-benzyl)-4-oxo-tetrahydro-thiopyran-3-carboxylic acid allyl ester

HRID 420264Notes

Reaction equation

[CH2:1]([O:4][C:5]([CH:7]1[C:12](=[O:13])[CH:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][S:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3].C([O-])([O-])=O.[K+].[K+].Br[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[C:32]([F:39])[CH:31]=1.CCCCCC.CCOC(C)=O>CC(C)=O>[CH2:1]([O:4][C:5]([C:7]1([CH2:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[C:32]([F:39])[CH:31]=2)[C:12](=[O:13])[CH:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][S:9][CH2:8]1)=[O:6])[CH:2]=[CH2:3]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-tert-butoxycarbonylamino-4-oxo-tetrahydro-thiopyran-3-carboxylic acid allyl ester (2.55 g, 8.08 mmol) in acetone (150 mL) was added K2CO3 (3.38 g, 24.2 mmol) and 4-bromomethyl-2-fluoro-1-nitro-benzene (2.12 g, 8.9 mmol) and the reaction mixture was stirred at 25° C. for 16 h. After dilution with water the product is extracted with EtOAc. Combined extracts were washed with brine, dried over MgSO4 and evaporated. The product obtained as a light yellow solid was suitable for use in the next step: TLC (hexane-EtOAc 1:3) Rf=0.26; HPLC RtA=2.31 min; ESIMS [M+NH4]+=486.

Workup

extractionAfter dilution with water the product is extracted with EtOAc
washCombined extracts were washed with brine
dry with materialdried over MgSO4
customevaporated
customThe product obtained as a light yellow solid
customHPLC RtA=2.31 min

Sources & evidence

ORD record: ord-90f4d31b6ed74d3098faf2a09a833331
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093406B2

Reaction notes

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