Trifluoroacetic acid → HCID 11132119, compound

HRID 1609388Notes

Reaction equation

HRID 1609388 reaction equation
[BH4-].[Na+].FC(F)(F)C(O)=O.CO[N:12]=[C:13]1[CH2:16][C@H:15]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C@H:14]1[CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>O1CCCC1>[CH3:34][C:31]([Si:28]([CH3:30])([CH3:29])[O:27][CH2:26][C@@H:14]1[C@@H:15]([CH2:17][O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[CH2:16][C@H:13]1[NH2:12])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 86747094HCID 86747094, compound

Product 1

HCID 11132119HCID 11132119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 186.3 g (4.9 mol) of sodium borohydride in 4 L of tetrahydrofuran (THF) was added (over a 30 minute period) 376 mL (4.9 mol) of trifluoroacetic acid (TFA), with ice water cooling to maintain temperature below 15° C. [2R, 3S]-2,3-bis(((1,1-Dimethylethyl)dimethylsilyl)oxymethyl)cyclobutanone-O-methyl oxime (400 g, 1.03 mol), from Step 1E, in 3 L of THF was added with ice water cooling to maintain the temperature below 20° C. After stirring the reaction mixture at ambient temperature overnight, it was concentrated, diluted with methylene chloride (3 L) and washed portionwise (with cooling) with 400 mL of brine. After filtration, the layers of the filtrate were separated and the aqueous layer was washed with methylene chloride. The combined methylene chloride solution was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give crude title compound which was taken on to the next step without purification.

Workup

  1. temperatureto maintain the temperature below 20° C
  2. concentrationwas concentrated
  3. additiondiluted with methylene chloride (3 L)
  4. washwashed portionwise
  5. temperature(with cooling) with 400 mL of brine
  6. filtrationAfter filtration
  7. customthe layers of the filtrate were separated
  8. washthe aqueous layer was washed with methylene chloride
  9. washThe combined methylene chloride solution was washed with brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-471de193a09847f685f20cee306d7873
Source dataset
uspto-grants-1995_03
Patent number
US05399775

Reaction notes

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