Trichloroacetyl isocyanate → HCID 12136226, compound

HRID 857958Notes

Reaction equation

HRID 857958 reaction equation
ClC(Cl)(Cl)C([N:5]=[C:6]=[O:7])=O.[CH3:10][O:11][C:12](=[O:58])/[CH:13]=[CH:14]\[C@H:15]([CH3:57])[C@H:16]([O:49][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:52])[CH3:51])[C@@H:17]([CH3:48])/[CH:18]=[C:19](/[CH3:47])\[CH2:20][C@H:21]([CH3:46])[C@@H:22]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[C@H:23]([CH3:37])[C@@H:24]([OH:36])[C@@H:25]([CH3:35])[CH2:26][O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[CH3:10][O:11][C:12](=[O:58])/[CH:13]=[CH:14]\[C@H:15]([CH3:57])[C@H:16]([O:49][Si:50]([C:53]([CH3:56])([CH3:55])[CH3:54])([CH3:51])[CH3:52])[C@@H:17]([CH3:48])/[CH:18]=[C:19](/[CH3:47])\[CH2:20][C@H:21]([CH3:46])[C@@H:22]([O:38][Si:39]([C:42]([CH3:43])([CH3:44])[CH3:45])([CH3:41])[CH3:40])[C@H:23]([CH3:37])[C@@H:24]([O:36][C:6]([NH2:5])=[O:7])[C@@H:25]([CH3:35])[CH2:26][O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 12136225HCID 12136225, compound

Product 1

HCID 12136226HCID 12136226, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trichloroacetyl isocyanate (106 mg, 0.56 mmol, 1.5 eq) is added to a solution of (2Z,4S,5S,6S,7Z,10S,11R,12R,13S,14S)-5,11-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13-hydroxy-4,6,8,10,12,14-hexamethyl-15-(phenylmethoxy)-2,7-pentadecadienoic acid methyl ester (266 mg, 0.37 mmol) in CH2Cl2 (5 mL) at 23° C. The mixture is stirred for 30 min. The solvent is removed. The residue is chromatographed (10% EtOAc in hexane) to give 208 mg (74%) of the desired compound as a white foam.

Workup

  1. customThe solvent is removed
  2. customThe residue is chromatographed (10% EtOAc in hexane)

Sources & evidence

ORD record
ord-a597b678b0e44caa885254edf844b324
Source dataset
uspto-grants-2006_12
Patent number
US07148218B2

Reaction notes

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