Pentafluorophenyl Trifluoroacetate → HCID 86650290, compound

HRID 1615860Notes

Reaction equation

HRID 1615860 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][C@:16]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)([CH3:18])[N:15]([CH2:27][C:28]([OH:30])=[O:29])[C:14](=[O:31])[C:9]21[CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(O[C:37]1[C:42]([F:43])=[C:41]([F:44])[C:40]([F:45])=[C:39]([F:46])[C:38]=1[F:47])=O>CN(C=O)C>[F:25][C:23]1[CH:24]=[C:19]([C@@:16]2([CH3:18])[N:15]([CH2:27][C:28](=[O:30])[O:29][C:37]3[C:38]([F:47])=[C:39]([F:46])[C:40]([F:45])=[C:41]([F:44])[C:42]=3[F:43])[C:14](=[O:31])[C:9]3([CH2:10][CH2:11][CH2:12][CH2:13]3)[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:17]2)[CH:20]=[C:21]([F:26])[CH:22]=1

Participants

4

Reactant 2

HCID 4327891Pentafluorophenyl TrifluoroacetateHCID 58118680HCID 58118680, compound2×

Product 1

HCID 86650290HCID 86650290, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of [(8R)-6-(tert-butoxycarbonyl)-8-(3,5-difluorophenyl)-8-methyl-10-oxo-6,9-diazaspiro[4.5]dec-9-yl]acetic acid (254 mg, 0.579 mmol, described in Intermediate 21) in DMF (2 mL) was added pentafluorophenyl trifluoroacetate (0.7 mL, 4.07 mmol). The reaction mixture was stirred for 4 h at ambient temperature, then partitioned between saturated aqueous NaHCO3 (30 mL) and EtOAc (50 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified on silica gel, eluting with a gradient of hexanes:EtOAc—100:0 to 0:100, to provide the title compound.

Workup

  1. custompartitioned between saturated aqueous NaHCO3 (30 mL) and EtOAc (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified on silica gel
  6. washeluting with a gradient of hexanes

Sources & evidence

ORD record
ord-86e3e108cf894135ab75170c51700e8e
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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