Triethylamine → HCID 22242968, compound

HRID 891751Notes

Reaction equation

HRID 891751 reaction equation
[Si:1]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:36])[N:29]([CH2:31][CH2:32][N:33]=[N+]=[N-])[CH3:30])[N:27]=2)[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:37]([C:40]1[CH:50]=[CH:49][C:43]([CH2:44][O:45][C:46](Cl)=[O:47])=[CH:42][CH:41]=1)([O-:39])=[O:38].C(N(CC)CC)C>CO.[OH-].[OH-].[Pd+2]>[Si:1]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:36])[N:29]([CH3:30])[CH2:31][CH2:32][NH:33][C:46]([O:45][CH2:44][C:43]3[CH:42]=[CH:41][C:40]([N+:37]([O-:39])=[O:38])=[CH:50][CH:49]=3)=[O:47])[N:27]=2)[CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 782054-Nitrobenzyl chloroformateHCID 22243019HCID 22243019, compound

Product 1

HCID 22242968HCID 22242968, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-t-butyldiphenylsilyloxy-1-{4-[N-(2-azidoethyl)-N-methyl-carbamoyl]-1,3-thiazol-2-yl}azetidine (1.05 g, 2.02 mmol) (obtained as described in Reference Example 58(2)) in methanol (60 ml) was subjected to catalytic hydrogenation in the presence of 20% palladium hydroxide on charcoal (1.05 g) at room temperature. After checking the completion of the reaction, the reaction mixture was filtered in order to remove the catalyst, and the filtrate concentrated under reduced pressure. To a solution of the obtained crude product in methylene chloride (52.3 ml) were added chloroformic acid p-nitrobenzyl ester (650.7 mg, 3.02 mmol) and triethylamine (0.42 ml, 3.01 mmol) in an ice bath. The mixture was stirred at room temperature for 1.5 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The obtained organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene:acetonitrile (2:1) as the eluant to afford 3-t-butyldiphenylsilyloxy-1-(4-{N-methyl-N-[2-(p-nitrobenzyloxycarbonylamino)-ethyl]carbamoyl}-1,3-thiazol-2-yl)azetidine (699.5 mg, yield 52%) as a pale yellow solid.

Workup

  1. customthe completion of the reaction
  2. filtrationthe reaction mixture was filtered in order
  3. customto remove the catalyst
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customTo a solution of the obtained crude product in methylene chloride (52.3 ml)
  6. customthe completion of the reaction
  7. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
  8. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-360451c11a044933b4755cf00b4d7ced
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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