Triphenylphosphine → Methyl 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-[(2S)-1-[(2-methylpropan-2-yl) oxy]propan-2-yl]oxy-benzoate

HRID 2425487Notes

Reaction equation

HRID 2425487 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]([C:5]1[N:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]([CH:19]=[C:20]([OH:22])[CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])=[N:9][CH:10]=1)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:43][C:44]([O:47][CH2:48][C@H:49](O)[CH3:50])([CH3:46])[CH3:45].CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:23][N:2]([CH3:1])[C:3]([C:5]1[N:6]=[CH:7][C:8]([O:11][C:12]2[CH:13]=[C:14]([CH:19]=[C:20]([O:22][C@@H:49]([CH3:50])[CH2:48][O:47][C:44]([CH3:46])([CH3:45])[CH3:43])[CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])=[N:9][CH:10]=1)=[O:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11557288(R)-1-tert-Butoxy-2-propanolHCID 59205093Methyl 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-hydroxy-benzoate

Product 1

HCID 59205102Methyl 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-[(2S)-1-[(2-methylpropan-2-yl) oxy]propan-2-yl]oxy-benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To methyl 3-[5-(dimethylcarbamoyl)pyrazin-2-yl]oxy-5-hydroxy-benzoate (10 g, 32 mmol) was added triphenylphosphine (10.3 g, 39.4 mmol), THF (100 mL) and (2R)-1-[(2-methylpropan-2-yl)oxy]propan-2-ol (CAS no. 136656-73-0) (5.21 g, 39.4 mmol). The resulting slurry was cooled to 0° C. and diethylazodicarboxylate (50% w/v in toluene, 13.7 mL, 39.4 mmol) was charged dropwise keeping the temperature below 10° C. After 2 hours the solvent was evaporated under reduced pressure and taken up with ethyl acetate (23 mL). A solid crashed out which was filtered and the mother liquors were evaporated under reduced pressure, taken up into ethyl acetate (23 mL) and isohexane (53 mL) and the resulting solid filtered, the mother liquors were evaporated under reduced pressure and the resulting residue was purified by flash chromatography eluting with 80% ethyl acetate/ 20% isohexane to afford the product (13.5 g).

Workup

  1. customthe temperature below 10° C
  2. customAfter 2 hours the solvent was evaporated under reduced pressure
  3. filtrationwas filtered
  4. customthe mother liquors were evaporated under reduced pressure
  5. filtrationthe resulting solid filtered
  6. customthe mother liquors were evaporated under reduced pressure
  7. customthe resulting residue was purified by flash chromatography
  8. washeluting with 80% ethyl acetate/ 20% isohexane

Sources & evidence

ORD record
ord-f8ac4487802647febbaae3a25222f552
Source dataset
uspto-grants-2011_06
Patent number
US07964725B2

Reaction notes

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