Hydrochloric Acid → HCID 86753165, compound

HRID 2395185Notes

Reaction equation

HRID 2395185 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]([CH2:28][C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:30])=[C:13]([O:26][CH3:27])[CH:14]=[C:15]([CH2:24][NH2:25])[C:16]=1[NH:17]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:39]1(=[O:46])[O:45][C:43](=[O:44])[CH2:42][CH2:41][CH2:40]1.N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1>[CH2:32]([O:31][C:29]([CH2:28][C:12]1[C:11]2[S:10][C:9]3[C:18](=[CH:19][CH:20]=[C:21]([O:22][CH3:23])[C:8]=3[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[N:17]([C:39](=[O:46])[CH2:40][CH2:41][CH2:42][C:43]([OH:45])=[O:44])[C:16]=2[C:15]([CH2:24][NH2:25])=[CH:14][C:13]=1[O:26][CH3:27])=[O:30])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7940Glutaric anhydrideHCID 131720845HCID 131720845, compound

Product 1

HCID 86753165HCID 86753165, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 360 mg (0.67 mmol) of benzyl (6-tert.-butoxycarbonyl-aminomethyl-3,7-dimethoxy-phenothiazin-4-yl)-acetate, 91.7 mg (0.80 mmol) of glutaric anhydride and 63.7 mg (0.80 mmol) of pyridine in 5 ml of toluene was treated with 10 mg of N,N-dimethylaminopyridine. The mixture was heated to 110° under argon for 48 hours and then poured into ice-water, whereupon the mixture was acidified with 1N hydrochloric acid and exhaustively extracted with methylene chloride. The organic phase was dried over magnesium sulphate and concentrated. The residue was chromatographed on silica gel with chloroform/methanol (9:1), whereupon 310 mg (71%) of 5-(4-benzyloxycarbonylmethyl-6-tert.-butoxycarbonyl-aminomethyl-3,7-dimethoxy-phenothiazin-10yl)-5-oxo-pentanoic acid were obtained as a white solid of m.p. 65°-68°.

Workup

  1. temperatureThe mixture was heated to 110° under argon for 48 hours
  2. extractionexhaustively extracted with methylene chloride
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel with chloroform/methanol (9:1)

Sources & evidence

ORD record
ord-f14ebf552adf49b38e7c0789a235cf0e
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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