Trifluoroacetic acid → HCID 68890052, compound

HRID 1760602Notes

Reaction equation

HRID 1760602 reaction equation
C(OC([C:6]1[N:7]([C@H:18]([CH3:28])[CH2:19][NH:20][C:21]([O:23]C(C)(C)C)=O)[C:8]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]1[C:9]=2[CH2:10][CH2:11][CH2:12]1)=O)C.FC(F)(F)C(O)=O>ClCCl>[CH3:28][C@@H:18]1[CH2:19][NH:20][C:21](=[O:23])[C:6]2[N:7]1[C:8]1[C:9]3[CH2:10][CH2:11][CH2:12][C:13]=3[CH:14]=[CH:15][C:16]=1[CH:17]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68888919HCID 68888919, compound

Product 1

HCID 68890052HCID 68890052, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-1-(2-tert-Butoxycarbonylamino-1-methyl-ethyl)-1,6,7,8-tetrahydro-1-aza-as-indacene-2-carboxylic acid ethyl ester (7.2 g, ˜17 mmol) was dissolved in dichloromethane (110 mL) and treated with trifluoroacetic acid (29 mL) at 0° C. After removal of the ice bath, the solution was stirred for 1 h, and evaporated under reduced pressure. The residue was dissolved in methanol (120 mL); after addition of saturated sodium bicarbonate solution (110 mL) and 2.6 g potassium carbonate the mixture was stirred for 20 h at room temperature. Water (100 mL) was added and the mixture was extracted with dichloromethane (2×100 mL). The organic layer was separated, washed with brine, dried (MgSO4), and evaporated. Crystallization from diethyl ether yielded the title compound as a colorless solid (2.6 g, 57%). EI-MS: m/e 240.2 (M+).

Workup

  1. customAfter removal of the ice bath
  2. customevaporated under reduced pressure
  3. dissolutionThe residue was dissolved in methanol (120 mL)
  4. additionafter addition of saturated sodium bicarbonate solution (110 mL) and 2.6 g potassium carbonate the mixture
  5. stirringwas stirred for 20 h at room temperature
  6. additionWater (100 mL) was added
  7. extractionthe mixture was extracted with dichloromethane (2×100 mL)
  8. customThe organic layer was separated
  9. washwashed with brine
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customCrystallization from diethyl ether

Sources & evidence

ORD record
ord-0adc2720af0e44d8939ce4b7efe62052
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

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