Potassium Hydroxide → HCID 131731652, compound

HRID 1618863Notes

Reaction equation

HRID 1618863 reaction equation
[CH:1](=[C:3]1[C:7]([C:14]2[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH:5]([CH3:21])[N:4]1[CH3:22])[CH3:2].[OH-].[K+].Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>CS(C)=O.C(OCC)(=O)C>[CH:1](=[C:3]1[C:7]([C:14]2[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=2)[O:20][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH:5]([CH3:21])[N:4]1[CH3:22])[CH3:2]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 79177tert-Butyl bromoacetateHCID 131731653HCID 131731653, compound

Product 1

HCID 131731652HCID 131731652, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

Product of Step 9 (1 g) was dissolved in dimethylsulfoxide (60 mL). To this, powdered potassium hydroxide (1 g) and tertiarybutyl bromoacetate (2.5 mL) was added. The reaction mixture was stirred under argon for 3 hr at 25° C. The reaction mixture was diluted with ethyl acetate (800 mL) and was extracted with water (twice at 200 mL each) and saturated sodium chloride in water (200 mL). The organic layer was dried on magnesium sulfate, was filtered, and was concentrated under vacuum. Crude product was loaded on a SNAP cartridge containing 100 g silica gel and eluted with a gradient of chloroform and methanol using the BIOTAGE® AB ISOLERA™ flash chromatography system. Fractions containing product were pooled and evaporated to obtain product of Step 10 as a red oil (0.26 g). 1H NMR (CDCl3): 1.3 δ (—CH—CH3 of isopropyl), 1.5 δ (—(CH3)3 of tertiarybutyl) 2.1 δ (3H, ═CH—CH3 of ethylidene) 2.9 δ (3H, —N—(CH3)), 2.8, 3.1, 3.5 δ (1H, 1H, 1H —CH2-CH—CH3 of isopropyl), 4.4 δ (1H, ═CH—CH3 of ethylidene), 4.5 (2H, —O—CH2-C(O)—) 6.8-7.5 δ (9H, phenyl rings). Mass spectrometry: m/z=408 (M+H).

Workup

  1. extractionwas extracted with water (twice at 200 mL each) and saturated sodium chloride in water (200 mL)
  2. customThe organic layer was dried on magnesium sulfate
  3. filtrationwas filtered
  4. concentrationwas concentrated under vacuum
  5. additioncontaining 100 g silica gel
  6. washeluted with a gradient of chloroform and methanol using the BIOTAGE® AB ISOLERA™ flash chromatography system
  7. additionFractions containing product
  8. customevaporated

Sources & evidence

ORD record
ord-ef6df9581dc849a0a2d0250172f8ab32
Source dataset
uspto-grants-2014_07
Patent number
US08771964B2

Reaction notes

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