Chloroform → HCID 59815128, compound

HRID 2235066Notes

Reaction equation

HRID 2235066 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]2[CH2:17][CH2:16]C(=O)[C@@H:14]2[C:19]2[CH:24]=[CH:23][C:22]([CH:25]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:21][CH:20]=2)=[CH:8][CH:9]=1)=[O:4].CCN(CC)CC.[CH:48]([Cl:51])(Cl)[Cl:49]>CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][C@H:13]2[CH2:17][CH2:16][C:48]([Cl:51])([Cl:49])[C@@H:14]2[C:19]2[CH:20]=[CH:21][C:22]([CH:25]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:23][CH:24]=2)=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 8471TriethylamineHCID 59815081HCID 59815081, compound

Product 1

HCID 59815128HCID 59815128, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Hydrazone 2 (prepared from 0.11 mmol of ketone as described above) in 1 mL CHCl3 was cannula transferred to a mixture of CuCl2 (107 mg, 0.80 mmol) and Et3N (50 μL, 0.36 mmol) in MeOH (1.2 mL), rinsing with 1 mL CHCl3. After 1 h, a solution of 10% conc. NH4OH/saturated NH4Cl (8 mL) was added and the mixture was extracted with CH2Cl2 (3×30 mL). The combined CH2Cl2 solution was dried (Na2SO4), filtered and evaporated. Purification by flash chromatography (0%→20% ethyl acetate/hexanes) gave compound 4 (34 mg, 49%).

Workup

  1. washrinsing with 1 mL CHCl3
  2. additiona solution of 10% conc. NH4OH/saturated NH4Cl (8 mL) was added
  3. extractionthe mixture was extracted with CH2Cl2 (3×30 mL)
  4. dry with materialThe combined CH2Cl2 solution was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash chromatography (0%→20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-68c81b55db944f37a200b32df8ee5c42
Source dataset
uspto-grants-2010_05
Patent number
US07713968B2

Reaction notes

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