Water → HCID 57950927, compound

HRID 1039659Notes

Reaction equation

HRID 1039659 reaction equation
[Si:1]([O:8][C@H:9]([C:30]1SC=CN=1)[C@@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:11][C:12]1[CH:20]=[C:19]([Cl:21])[C:15]2[O:16][CH2:17][O:18][C:14]=2[CH:13]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].FC(F)(F)S(OC)(=O)=[O:38].[BH4-].[Na+].O>CC#N.CCOC(C)=O.CCOCC.[Hg](Cl)Cl>[Si:1]([O:8][C@H:9]([CH:30]=[O:38])[C@@H:10]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:27])([CH3:28])[CH3:26])[CH2:11][C:12]1[CH:20]=[C:19]([Cl:21])[C:15]2[O:16][CH2:17][O:18][C:14]=2[CH:13]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

9

Reactant 4

HCID 962WaterHCID 9526Methyl triflateHCID 4311764Sodium borohydrideHCID 86635705HCID 86635705, compound

Product 1

HCID 57950927HCID 57950927, compound

Reagents, catalysts & solvents 4

HCID 24085Mercuric ChlorideCatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution tert-butyl (1S,2S)-1-(tert-butyldimethylsilyloxy)-3-(7-chlorobenzo[d][1,3]dioxol-5-yl)-1-(thiazol-2-yl)propan-2-ylcarbamate (1.85 g, 3.51 mmol) in MeCN (14 mL) was treated with 4A mol. seives and was allowed to stir at RT for 10 minutes. Methyl trifluoromethanesulfonate (0.464 ml, 4.21 mmol) was added, and the reaction mixture was allowed to stir for 30 minutes. The reaction mixture was then concentrated under reduced pressure, and the crude residual material was dissolved in MeOH (14 mL), and cooled to 0° C. The mixture was then treated with sodium borohydride (0.398 g, 10.5 mmol) and allowed to warm to RT and stir for an additional 20 minutes. The reaction mixture was diluted with EtOAc, filtered through celite and concentrated under reduced pressure. The residue was dissolved in ACN (10 mL) and water (4 mL) and was treated with mercury(II) chloride (0.953 g, 3.51 mmol). After stirring for 30 minutes the reaction mixture was diluted with ether and filtered through a short plug of silica. The filtrate was then concentrated under reduced pressure and the crude residue was purified by column chromatography yielding tert-butyl (2S,3S)-3-(tert-butyldimethylsilyloxy)-1-(7-chlorobenzo[d][1,3]dioxol-5-yl)-4-oxobutan-2-ylcarbamate.

Workup

  1. stirringto stir for 30 minutes
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. dissolutionthe crude residual material was dissolved in MeOH (14 mL)
  4. temperaturecooled to 0° C
  5. temperatureto warm to RT
  6. stirringstir for an additional 20 minutes
  7. filtrationfiltered through celite and
  8. concentrationconcentrated under reduced pressure
  9. dissolutionThe residue was dissolved in ACN (10 mL)
  10. stirringAfter stirring for 30 minutes the reaction mixture
  11. filtrationfiltered through a short plug of silica
  12. concentrationThe filtrate was then concentrated under reduced pressure
  13. customthe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-4253c19b866b4a8786791f0937f6af0e
Source dataset
uspto-grants-2013_10
Patent number
US08552181B2

Reaction notes

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