Triethylamine → HCID 11517221, compound

HRID 1766970Notes

Reaction equation

HRID 1766970 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]([NH:5][C@@H:6]1[CH2:9][NH:8][C@H:7]1[CH3:10])=[O:4].C(N(CC)CC)C.[C:20]([C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])[C:32]=1[OH:33])[C:27](Cl)=[O:28])([CH3:23])([CH3:22])[CH3:21]>ClCCl>[C:34]([C:31]1[CH:30]=[C:26]([CH:25]=[C:24]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:32]=1[OH:33])[C:27]([N:8]1[CH2:9][C@@H:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:11])[F:12])[C@@H:7]1[CH3:10])=[O:28])([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chlorideHCID 58887416HCID 58887416, compound

Product 1

HCID 11517221HCID 11517221, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(2S,3R)-2,2,2-trifluoro-N-(2-methyl-azetidin-3-yl)-acetamide (1,04 g, 4,74 mmoles) hydrochloride was dissolved in dichloromethane (30 ml) and triethylamine (2,7 ml) was added, the mixture stirred for 10 minutes at room temperature, cooled to 0° C. and a solution of 3,5-di-tert-butyl-4-hydroxy-benzoyl chloride (1,16 g, 4,3 mmoles) in dichloromethane (20 ml) was added. The reaction mixture was stirred at room temperature overnight, then poured on ice, the phases were separated, the aqeous phase extracted with dichloromethane and the combined organic phases were dried over magnesium sulfate, filtered and evaporated to dryness to give 1,42 g (80% of theoretical yield) of N-[1-(3,5-di-tert-butyl-4-hydroxy-benzoyl)-(2S,3R)-2-methyl-azetidin-3-yl]-2,2,2-trifluoro-acetamide.

Workup

  1. temperaturecooled to 0° C.
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. additionpoured on ice
  4. customthe phases were separated
  5. extractionthe aqeous phase extracted with dichloromethane
  6. dry with materialthe combined organic phases were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-7d1afe39d286437784a68ecf69962719
Source dataset
uspto-grants-2007_06
Patent number
US07232812B2

Reaction notes

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