Trichloroacetyl isocyanate → HCID 86760332, compound

HRID 857968Notes

Reaction equation

HRID 857968 reaction equation
[CH3:1][O:2][C:3](=[O:45])/[CH:4]=[CH:5]\[C@H:6]([CH3:44])[C@H:7]([O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[C@@H:8]([CH3:35])[CH2:9][N:10]([C:12](=[O:34])[C@H:13]([CH3:33])[C@@H:14]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[C@H:15]([CH3:24])[C@@H:16]([OH:23])[C@@H:17]([CH3:22])/[CH:18]=[CH:19]\[CH:20]=[CH2:21])[CH3:11].ClC(Cl)(Cl)[C:48]([N:50]=C=O)=[O:49]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:45])/[CH:4]=[CH:5]\[C@H:6]([CH3:44])[C@H:7]([O:36][Si:37]([C:40]([CH3:43])([CH3:41])[CH3:42])([CH3:38])[CH3:39])[C@@H:8]([CH3:35])[CH2:9][N:10]([C:12](=[O:34])[C@H:13]([CH3:33])[C@@H:14]([O:25][Si:26]([C:29]([CH3:30])([CH3:31])[CH3:32])([CH3:27])[CH3:28])[C@H:15]([CH3:24])[C@@H:16]([O:23][C:48]([NH2:50])=[O:49])[C@@H:17]([CH3:22])/[CH:18]=[CH:19]\[CH:20]=[CH2:21])[CH3:11]

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 86760333HCID 86760333, compound

Product 1

HCID 86760332HCID 86760332, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2Z,4S,5S,6S)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7-[[(2R,3S,4R,5S,6S,7Z)-3-[[(1, 1-dimethylethyl)dimethylsilyl]oxy]-5-hydroxy-2,4,6-trimethyl-1-oxo-7,9-decadienyl]methylamino]-4,6-dimethyl-2-heptenoic acid methyl ester (1.8 g, 2.7 mmol) in CH2Cl2 (10 mL) at room temperature, is added trichloroacetyl isocyanate (763 mg, 4.05 mmol) in one portion. The mixture is stirred at room temperature for 1 h, and concentrated in vacuo. The residue is dissolved in MeOH (10 mL), and then K2CO3 (0.4 g) is added. After stirring at room temperature for 2 h, the mixture is concentrated in vacuo, then purified by column chromatography with silica gel eluted with hexane/EtOAc (70/30) to give the desired compound (1.77 g, 92.4%) as a colorless glassy solid.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in MeOH (10 mL)
  3. additionK2CO3 (0.4 g) is added
  4. stirringAfter stirring at room temperature for 2 h
  5. concentrationthe mixture is concentrated in vacuo
  6. custompurified by column chromatography with silica gel
  7. washeluted with hexane/EtOAc (70/30)

Sources & evidence

ORD record
ord-6607f3b5ef8546f58ef9dc663571f211
Source dataset
uspto-grants-2006_12
Patent number
US07148218B2

Reaction notes

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