Benzyl Alcohol → HCID 131720852, compound

HRID 2395165Notes

Reaction equation

HRID 2395165 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:9]=1[S:10][C:11]1[C:12]([CH2:25][C:26]([OH:28])=[O:27])=[CH:13][CH:14]=[C:15]([CH2:23][NH2:24])[C:16]=1[N:17]2[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:29](O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([C:8]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:9]=1[S:10][C:11]1[C:12]([CH2:25][C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[CH:13][CH:14]=[C:15]([CH2:23][NH2:24])[C:16]=1[N:17]2[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 516892Sodium BicarbonateHCID 67644795HCID 67644795, compound

Product 1

HCID 131720852HCID 131720852, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

20 mg of N,N-dimethylaminopyridine and a solution of 455 mg (2.2 mmol) of N,N-dicyclohexylcarbodiimide in 5 ml of methylene chloride were added while cooling with ice to a solution of 801 mg (2.0 mmol) of (6-tert-butoxycarbonyl-aminomethyl-10-methyl-phenothiazin-4-yl)-acetic acid and 324.5 mg (3.0 mmol) of benzyl alcohol in methylene chloride. The reaction mixture was stirred at 0° for 15 minutes, brought slowly to room temperature, stirred for 2 hours and then poured into ice and saturated sodium hydrogen carbonate solution, whereupon the mixture was extracted three times with methylene chloride. The combined organic phases were dried over magnesium sulphate and evaporated. The residue was chromatographed on 100 g of silica gel with ethyl acetate/hexane (3:2), whereupon 730 mg (74.4%) of benzyl (6-tert.-butoxycarbonyl-aminomethyl-10-methyl-phenothiazin-4-yl)-acetate were obtained as an amorphous solid. MS: 490 (M+ 78), 434(100), 416(22), 390(20), 91(60).

Workup

  1. custombrought slowly to room temperature
  2. stirringstirred for 2 hours
  3. extractionwas extracted three times with methylene chloride
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on 100 g of silica gel with ethyl acetate/hexane (3:2)

Sources & evidence

ORD record
ord-09968f1540274d89a05c29c266f7918f
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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