Trifluoroacetic acid → HCID 67206190, compound

HRID 2041690Notes

Reaction equation

HRID 2041690 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[N:15]=[N:16][N:17]([CH2:19][CH2:20][O:21][Si](C(C)(C)C)(C)C)[CH:18]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:29]C(=O)OC(C)(C)C)[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[N:15]=[N:16][N:17]([CH2:19][CH2:20][OH:21])[CH:18]=3)=[CH:11][CH:12]=2)[C@H:7]([NH2:29])[CH2:6][C@@H:5]1[CH3:37])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68184856HCID 68184856, compound

Product 1

HCID 67206190HCID 67206190, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl {(2S,4R)-1-acetyl-6-[1-(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-1H-1,2,3-triazol-4-yl]-2-methyl-1,2,3,4-tetrahydro-4-quinolinyl}carbamate (for a preparation see intermediate 46) (599 mg, 1.131 mmol) in dichloromethane (DCM) (20 mL) was treated with trifluoroacetic acid (TFA) (5.00 mL) and the resulting reaction mixture was stirred for 1 h at room temperature then concentrated in vacuovacuo. Purification of the residue on SP4 using a 50 G silica cartridge (gradient:0 to 12% MeOH in DCM) gave 2-{4-[(2S,4R)-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]-1H-1,2,3-triazol-1-yl}ethanol (396 mg, 0.885 mmol, 78% yield) as a yellow solid.

Workup

  1. customthe resulting reaction mixture
  2. concentrationthen concentrated in vacuovacuo
  3. customPurification of the residue on SP4

Sources & evidence

ORD record
ord-e217725def2b42b791418c59359e79ce
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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