Methyl iodide → HCID 131729364, compound

HRID 420274Notes

Reaction equation

HRID 420274 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:41]=[CH:42][CH:43]=1)[CH2:8][N:9]1[C@@H:17]2[C@H:12]([C@H:13]([CH2:20][C:21]3[CH:26]=[C:25]([CH2:27][C@H:28]([OH:33])[C:29]([F:32])([F:31])[F:30])[C:24]([N:34]=[CH:35][N:36]([CH3:38])[CH3:37])=[C:23]([F:39])[CH:22]=3)[CH2:14][S:15](=[O:19])(=[O:18])[CH2:16]2)[O:11][C:10]1=[O:40])([CH3:4])([CH3:3])[CH3:2].CI.[C:46]([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]([CH:41]=[CH:42][CH:43]=1)[CH2:8][N:9]1[C@@H:17]2[C@H:12]([C@H:13]([CH2:20][C:21]3[CH:26]=[C:25]([CH2:27][C@H:28]([O:33][CH3:46])[C:29]([F:31])([F:32])[F:30])[C:24]([N:34]=[CH:35][N:36]([CH3:37])[CH3:38])=[C:23]([F:39])[CH:22]=3)[CH2:14][S:15](=[O:18])(=[O:19])[CH2:16]2)[O:11][C:10]1=[O:40])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 131729363HCID 131729363, compound

Product 1

HCID 131729364HCID 131729364, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of N′-[4-[(3aR*,7S*,7aS*)-3-(3-tert-butyl-benzyl)-2,5,5-trioxo-octahydro-1-oxa-5lambda*6*-thia-3-aza-inden-7-ylmethyl]-2-fluoro-6-((S)-3,3,3-trifluoro-2-hydroxy-propyl)-phenyl]-N,N-dimethyl-formamidine (0.095 g, 0.144 mmol) in anhydrous DMF was added under argon NaH (0.008 g, 0.34 mmol, 95%) and after 20 min stirring methyliodide (0.028 mL, 0.44 mmol). The reaction mixture was stirred for 2 h at 25° C. After addition of saturated aq. NaHCO3 solution the title compound was extracted with EtOAc. The crude compound, a light yellow oil, was used as such in the next step: TLC (EtOAc) Rf=0.47; HPLC RtA=2.06 min; ESIMS [M+H]+=642.

Sources & evidence

ORD record
ord-cd8de5525e644c7fb33d1699ffb91083
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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