Triethylamine → HCID 131728632, compound

HRID 1359998Notes

Reaction equation

HRID 1359998 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH2:20]([OH:27])[C:21]([NH2:26])([CH2:24][OH:25])[CH2:22][OH:23].Cl.[OH:29][C:30]([CH:32]([C:34]1[CH:47]=[CH:46][CH:45]=[C:36]([C:37]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:38])[CH:35]=1)[CH3:33])=[O:31].C(OCC)(=O)C>C(Cl)(Cl)Cl>[C:1]([NH:8][CH2:9][C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2].[CH2:20]([OH:27])[C:21]([NH2:26])([CH2:24][OH:25])[CH2:22][OH:23].[OH:31][C:30]([CH:32]([C:34]1[CH:47]=[CH:46][CH:45]=[C:36]([C:37]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:38])[CH:35]=1)[CH3:33])=[O:29]

Participants

6

Reactant 4

HCID 8471Triethylamine5×HCID 8857Ethyl AcetateHCID 78288N-(tert-butoxycarbonyl)glycine3×HCID 131728633HCID 131728633, compound

Product 1

HCID 131728632HCID 131728632, compoundYield 149.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent4×

Procedure

In 1 ml of chloroform, 133 mg (0.76 mmol) of Boc-glycine was dissolved, and 106 μl (0.76 mmol) of triethylamine and Mpt-Cl 98 mg (0.76 mmol)/1 ml chloroform were added thereto under ice-cooling, followed by stirring for 10 minutes. Thereafter, 433 mg (0.5 mmol) of the tris(hydroxymethyl)aminomethane-ketoprofen hydrochloride obtained in Example 31/70 μl (0.5 mmol) of triethylamine/2 ml of chloroform, and 106 μl (0.76 mmol) of triethylamine were gradually added thereto by dividing into 4 portions. After stirring at room temperature for 1 hour, 106 μl (0.76 mmol) of triethylamine was further added thereto under ice-cooling, and a mixed acid anhydride of Boc-glycine activated by dissolving 131 mg (0.75 mmol) of Boc-glycine in 1 ml chloroform and by adding, under ice-cooling, 105 μl (0.75 mmol) of triethylamine and 95 mg (0.75 mmol) Mpt-Cl/1 ml chloroform was added thereto, and the mixture was stirred at room temperature overnight. Ethyl acetate was added thereto, followed by separation by washing twice with 5% citric acid, water, twice with 5% sodium hydrogen carbonate, water and saturated brine consecutively. After dehydration drying with sodium sulfate, ethyl acetate was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2) to give 411 mg of the titled compound (yield 55%). The structure was identified by 1H-NMR (CDCl3).

Workup

  1. temperatureunder ice-cooling
  2. stirringAfter stirring at room temperature for 1 hour
  3. temperatureunder ice-cooling
  4. additionby adding, under ice-
  5. temperaturecooling
  6. stirringthe mixture was stirred at room temperature overnight
  7. customfollowed by separation
  8. washby washing twice with 5% citric acid, water, twice with 5% sodium hydrogen carbonate, water and saturated brine consecutively
  9. dry with materialAfter dehydration drying with sodium sulfate, ethyl acetate
  10. customwas evaporated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:2)

Sources & evidence

ORD record
ord-2bb41f9705f64da79e1acd1ef7628191
Source dataset
uspto-grants-2011_02
Patent number
US07879817B2

Reaction notes

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