Diazomethane → HCID 86753154, compound

HRID 2395164Notes

Reaction equation

HRID 2395164 reaction equation
[N+](=[CH2:3])=[N-].[C:4]([O:8][C:9]([C:11]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:12]=1[S:13][C:14]1[C:15]([CH2:28][C:29]([OH:31])=[O:30])=[CH:16][CH:17]=[C:18]([CH2:26][NH2:27])[C:19]=1[N:20]2[CH3:25])=[O:10])([CH3:7])([CH3:6])[CH3:5]>C(Cl)Cl>[C:4]([O:8][C:9]([C:11]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:12]=1[S:13][C:14]1[C:15]([CH2:28][C:29]([O:31][CH3:3])=[O:30])=[CH:16][CH:17]=[C:18]([CH2:26][NH2:27])[C:19]=1[N:20]2[CH3:25])=[O:10])([CH3:7])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 67644795HCID 67644795, compound

Product 1

HCID 86753154HCID 86753154, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 ml of diazomethane solution (~0.3N in diethyl ether) was added dropwise while cooling with ice to a solution of 80 mg (0.19 mmol) of (6-tert-butoxycarbonyl-aminomethyl-10-methyl-phenothiazin-4-yl)-acetic acid in 4 ml of methylene chloride. The reaction mixture was brought to room temperature, stirred for 1.5 hours and evaporated. The residue was crystallized from ethyl acetate/hexane, whereupon, after drying in a high vacuum, 72 mg (91%) of methyl (6-tert-butoxycarbonyl-aminomethyl-10-methyl-phenothiazin-4-yl)-acetate were obtained as a white solid. MS 414 (M+, 64), 358 (100), 343 (15), 314 (15), 238 (15), 57 (16).

Workup

  1. customwas brought to room temperature
  2. customevaporated
  3. customThe residue was crystallized from ethyl acetate/hexane, whereupon
  4. customafter drying in a high vacuum

Sources & evidence

ORD record
ord-9b937db4d61242f58c92d1a6a9314442
Source dataset
uspto-grants-1998_09
Patent number
US05811548

Reaction notes

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