Benzyl Alcohol → HCID 86753158, compound

HRID 2395178Notes

Reaction equation

HRID 2395178 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[C:18]2[C:9]=1[S:10][C:11]1[C:12]([CH2:29][C:30]([OH:32])=[O:31])=[C:13]([O:27][CH3:28])[CH:14]=[C:15]([CH2:25][NH2:26])[C:16]=1[N:17]2[CH3:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:33](O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[C:1]([O:5][C:6]([C:8]1[C:21]([O:22][CH3:23])=[CH:20][CH:19]=[C:18]2[C:9]=1[S:10][C:11]1[C:12]([CH2:29][C:30]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])=[C:13]([O:27][CH3:28])[CH:14]=[C:15]([CH2:25][NH2:26])[C:16]=1[N:17]2[CH3:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 244Benzyl AlcoholHCID 86753159HCID 86753159, compound

Product 1

HCID 86753158HCID 86753158, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 158 mg (0.77 mmol) of N,N-dicyclohexylcarbodiimide in methylene chloride was added dropwise to an ice-cooled solution of 3.20 mg (0.695 mmol) of (6-tert.-butoxycarbonyl-aminomethyl-3,7-dimethoxy-10-methyl-phenothiazin-4-yl)-acetic acid, 90.2 mg (0.84 mmol) of benzyl alcohol and 20 mg of N,N-dimethylaminopyridine in 2.5 ml of methylene chloride. The reaction mixture was stirred at room temperature overnight and filtered. The filter residue was washed with methylene chloride. The combined filtrates were washed with saturated sodium bicarbonate solution, dried over magnesium sulphate and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:4), whereupon, after recrystallization from ethanol and drying, 280 mg (73.3%) of benzyl (6-tert.-butoxycarbonyl-aminomethyl-3,7-dimethoxy-10-methyl-phenothiazin-4-yl)-acetate were obtained as white crystals of m.p. 131°-132°.

Workup

  1. filtrationfiltered
  2. washThe filter residue was washed with methylene chloride
  3. washThe combined filtrates were washed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel with ethyl acetate/hexane (1:4), whereupon
  7. customafter recrystallization from ethanol
  8. customdrying

Sources & evidence

ORD record
ord-a986a16aa17f45cb8d82e6c8234e8b12
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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