2,2-Dimethoxypropane → HCID 66638811, compound

HRID 1094452Notes

Reaction equation

HRID 1094452 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[F:29])[CH:10]([OH:21])[CH2:11][C:12]1[N:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].B(F)(F)F.CCOCC.CO[C:41](OC)([CH3:43])[CH3:42]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[C@H:9]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[CH:10]([CH2:11][C:12]2[N:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])[O:21][C:41]1([CH3:43])[CH3:42])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 64952,2-DimethoxypropaneHCID 8000Boron trifluoride etherateHCID 66638711HCID 66638711, compound

Product 1

HCID 66638811HCID 66638811, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-[3-tert-Butoxycarbonylamino-4-(2-fluoro-phenyl)-2-hydroxy-butyl]-nicotinic acid (13 g, 32 mmol) in 500 mL of 2,2-dimethoxypropane and 500 mL of acetone at 0° C. is added boron trifluoride diethyl etherate (3.2 mL, 25 mmol). The reaction is heated at 40° C. overnight after which time the solvent is removed under reduced pressure. The resultant residue is then partitioned between dichloromethane and water and extracted with dichloromethane. The combined organic phases are dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel flash column chromatography gives the title compound.

Workup

  1. customis removed under reduced pressure
  2. customThe resultant residue is then partitioned between dichloromethane and water
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel flash column chromatography

Sources & evidence

ORD record
ord-3c27dc973bbb4baf8c70bd847c06b06f
Source dataset
uspto-grants-2012_03
Patent number
US08133907B2

Reaction notes

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