Trifluoroacetic acid → HCID 53629823, compound

HRID 889602Notes

Reaction equation

HRID 889602 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][CH2:8][N:9]([S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH:23]([C:30](=[O:37])[NH:31][C:32]2[S:33][CH:34]=[N:35][N:36]=2)[CH2:24][CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:10][CH2:11][O:12][CH3:13])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:25]1([CH2:24][CH:23]([C:20]2[CH:21]=[CH:22][C:17]([S:14]([N:9]([CH2:10][CH2:11][O:12][CH3:13])[CH2:8][CH2:7][C:6]([OH:38])=[O:5])(=[O:16])=[O:15])=[CH:18][CH:19]=2)[C:30](=[O:37])[NH:31][C:32]2[S:33][CH:34]=[N:35][N:36]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67025033HCID 67025033, compound

Product 1

HCID 53629823HCID 53629823, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 75 mg (0.133 mmol) of title F compound, 3-[{4-[2-cyclopentyl-1-([1,3,4]thiadiazol-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-(2-methoxy-ethyl)-amino]-propionic acid tert-butyl ester is added 2 mL of DCM and 0.5 mL of trifluoroacetic acid. The reaction mixture is stirred at ambient temperature for one hour. The reaction is evaporated to a brownish resin and subsequently dissolved in ether and decanted from some insoluble material. The organic layer is evaporated to a light orange resin which is dissolved in 2 mL methanol in a 50 mL round bottom flask. Aqueous potassium hydroxide (0.265 mL of 0.5094 M potassium hydroxide solution) is added and stirred for 30 min. The methanol is evaporated, 8 mL of water added, and the mixture lyophilized to afford 3-[{4-[2-cyclopentyl-1-([1,3,4]thiadiazol-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-(2-methoxy-ethyl)-amino]-propionic acid as a light orange-brown solid: 1H NMR (400 MHz, DMSO-d6) δ 1.1 (m, 1H), 1.4 (m, 1H), 1.6 (m, 2H), 1.7 (ddd, J=13.1, 6.9, 6.7 Hz, 2H), 2.1 (ddd, J=11.2, 8.2, 7.8, 2H), 3.2 (s, 2H), 3.2 (m, 3H), 3.7 (t, J=7.5 Hz, 1H), 7.56 (d, J=8.3, 2H), 7.63 (d, J=8.3 Hz, 2H), 8.58 (s, 1H); L/MS 511 (M+1), 509 (M−1). EC50 in primary enzyme assay 50 μM.

Workup

  1. customThe reaction is evaporated to a brownish resin
  2. dissolutionsubsequently dissolved in ether
  3. customdecanted from some insoluble material
  4. customThe organic layer is evaporated to a light orange resin which
  5. dissolutionis dissolved in 2 mL methanol in a 50 mL round bottom flask
  6. additionAqueous potassium hydroxide (0.265 mL of 0.5094 M potassium hydroxide solution) is added
  7. stirringstirred for 30 min
  8. customThe methanol is evaporated
  9. addition8 mL of water added

Sources & evidence

ORD record
ord-0f83783f95c64dc88a7d46cc14d66b48
Source dataset
uspto-grants-2012_08
Patent number
US08252931B2

Reaction notes

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