Water → HCID 86753164, compound

HRID 2395187Notes

Reaction equation

HRID 2395187 reaction equation
CI.N12CCCN=C1CCCC[CH2:4]2.[CH2:14]([O:21][C:22]([CH2:24][C:25]1[C:38]2[S:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([O:46][CH3:47])[C:35]=3[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[N:30]([C:48](=[O:55])[CH2:49][CH2:50][CH2:51][C:52]([OH:54])=[O:53])[C:29]=2[C:28]([CH2:56][NH2:57])=[CH:27][C:26]=1[O:58][CH3:59])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:14]([O:21][C:22]([CH2:24][C:25]1[C:38]2[S:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([O:46][CH3:47])[C:35]=3[C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40])[N:30]([C:48](=[O:55])[CH2:49][CH2:50][CH2:51][C:52]([O:54][CH3:4])=[O:53])[C:29]=2[C:28]([CH2:56][NH2:57])=[CH:27][C:26]=1[O:58][CH3:59])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86753165HCID 86753165, compound

Product 1

HCID 86753164HCID 86753164, compoundYield 88.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

103 mg (0.726 mmol) of methyl iodide and 110 mg (0.726 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene were added while cooling with ice to a solution of 430 mg (0.66 mmol) of 5-(4-benzyloxycarbonylmethyl-6-tert.-butoxycarbonyl-aminomethyl-3,7-dimethoxy-phenothiazin-10-yl)-5-oxo-pentanoic acid in 15 ml of N,N-dimethylformamide. The reaction mixture was stirred firstly at room temperature and then at 40°, then cooled and finally poured into water and ethyl acetate. The organic phase was extracted twice with water, dried over magnesium sulphate and concentrated. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:1), whereupon, after drying, 390 mg (88%) of methyl 5-(4-benzyloxycarbonylmethyl-6-tert.-butoxycarbonyl-aminomethyl-3,7-dimethoxy-phenothiazin-10-yl)-5-oxo-pentanoate were obtained as a white amorphous foam. MS (FAB): 664 (M+).

Workup

  1. temperatureat 40°, then cooled
  2. extractionThe organic phase was extracted twice with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel with ethyl acetate/hexane (1:1), whereupon
  6. customafter drying

Sources & evidence

ORD record
ord-f2b1ec69b43144ee9ddc2c4b72a7299c
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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