Trifluoroacetic acid → HCID 68840776, compound

HRID 1983564Notes

Reaction equation

HRID 1983564 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([C@@H:15]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][N:16]2C(OC(C)(C)C)=O)=[O:14])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13]([C@@H:15]2[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][NH:16]2)=[O:14])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131727457HCID 131727457, compound

Product 1

HCID 68840776HCID 68840776, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of step 1 was dissolved in methylene chloride (40 mL) and treated with trifluoroacetic acid (20 mL). After stirring for 2.5 hours the reaction was concentrated and the residue was partitioned between methylene chloride and aqueous sodium bicarbonate solution. The organic layer was removed and the aqueous layer was further basified with concentrated ammonium hydroxide (ca., 20 mL) and extracted with additional methylene chloride. The combined organic layers were dried (sodium sulfate) and concentrated. The resulting tacky, golden solid was triturated with diethyl ether and vacuum oven dried to afford 8.34 g (86%) of product as colorless platelets: 1H NMR (CDCl3) δ 9.25 (s, 1H), 7.54-7.48 (m, 2H), 7.26-7.04 (m, 6H), 4.10-3.98 (m, 2H), 3.67 (dd, J=10.4, 5.5 Hz, 1H), 3.35 (dd, J=16.4, 5.5 Hz, 1H), 2.90 (dd, J=16.4, 10.4 Hz, 1H), 2.57 (t, J=7.6 Hz, 2H), 1.64-1.54 (m, 2H), 1.39-1.24 (m, 4H), 0.88 (t, J=6.8 Hz 3H) ppm.

Workup

  1. concentrationwas concentrated
  2. customthe residue was partitioned between methylene chloride and aqueous sodium bicarbonate solution
  3. customThe organic layer was removed
  4. extractionextracted with additional methylene chloride
  5. dry with materialThe combined organic layers were dried (sodium sulfate)
  6. concentrationconcentrated
  7. customThe resulting tacky, golden solid was triturated with diethyl ether and vacuum oven
  8. customdried

Sources & evidence

ORD record
ord-e1a9113bf3a94af994816edbf5849194
Source dataset
uspto-grants-2009_06
Patent number
US07541466B2

Reaction notes

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