Cyclohexaneacetic acid → HCID 86760455, compound

HRID 459071Notes

Reaction equation

HRID 459071 reaction equation
[CH:1]1([CH2:7][C:8]([OH:10])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:38][C:39]([Si:42]([CH3:78])([CH3:77])[O:43][C@H:44]([C@@H:55]([CH3:76])[CH2:56]/[C:57](/[CH3:75])=[CH:58]\[C@H:59]([CH3:74])[C@@H:60]([O:66][Si:67]([C:70]([CH3:73])([CH3:72])[CH3:71])([CH3:69])[CH3:68])[C@@H:61]([CH3:65])[CH2:62][NH:63][CH3:64])[C@H:45]([CH3:54])[C@@H:46]([OH:53])[C@@H:47]([CH3:52])/[CH:48]=[CH:49]\[CH:50]=[CH2:51])([CH3:41])[CH3:40].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:71][C:70]([Si:67]([CH3:68])([CH3:69])[O:66][C@H:60]([C@@H:59]([CH3:74])/[CH:58]=[C:57](/[CH3:75])\[CH2:56][C@H:55]([CH3:76])[C@@H:44]([O:43][Si:42]([C:39]([CH3:41])([CH3:40])[CH3:38])([CH3:78])[CH3:77])[C@H:45]([CH3:54])[C@@H:46]([OH:53])[C@@H:47]([CH3:52])/[CH:48]=[CH:49]\[CH:50]=[CH2:51])[C@@H:61]([CH3:65])[CH2:62][N:63]([CH3:64])[C:8](=[O:10])[CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([CH3:73])[CH3:72]

Participants

6

Reactant 4

HCID 21363Cyclohexaneacetic acidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 86587926HCID 86587926, compound

Product 1

HCID 86760455HCID 86760455, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
23 °C

Procedure

A DMF (2 mL) solution of cyclohexaneacetic acid (30.2 mg, 0.222 mmol) and BOP (131 mg, 0.296 mmol) is added to the stirred DMF (3 mL) solution of (3Z,5S,6S,7R,8R,9S,11Z,13S,14R,15S)-8,14-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5,7,9,11,13,15-hexamethyl-16-(methylamino)-1,3,11-hexadecatrien-6-ol (90 mg, 0.148 mmol) and DIEA (77 μL, 0.444 mmol) dropwise at 0° C. The solution is warmed up to 23° C. and stirred for an additional 1 hour. DMF is removed in vacuo and the residue is dissolved in EtOAc (10 mL). The organic solution is washed with H2O (1×10 mL) and brine (1×10 mL). The aqueous layer is extracted with Et2O (3×20 mL) and the combined extracts are dried (Na2SO4) and concentrated. Chromatography (SiO2, 0–30% EtOAc-hexanes gradient elution) provided the desired compound (70 mg, 65%). HRMS: ESI m/z 734.5906 (M+H+), Calcd. 734.5939.

Workup

  1. customDMF is removed in vacuo
  2. dissolutionthe residue is dissolved in EtOAc (10 mL)
  3. washThe organic solution is washed with H2O (1×10 mL) and brine (1×10 mL)
  4. extractionThe aqueous layer is extracted with Et2O (3×20 mL)
  5. dry with materialthe combined extracts are dried (Na2SO4)
  6. concentrationconcentrated
  7. washChromatography (SiO2, 0–30% EtOAc-hexanes gradient elution)

Sources & evidence

ORD record
ord-c362d3d0f0a547c490d2cbeda1cf5128
Source dataset
uspto-grants-2007_03
Patent number
US07192980B2

Reaction notes

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