Trifluoroacetic acid → HCID 10070444, compound

HRID 1768484Notes

Reaction equation

HRID 1768484 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C:11]([CH2:25]CC(O)=O)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1.[Si]([O:37][NH2:38])(C(C)(C)C)(C)C.CCN=C=NCCCN(C)C.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C.F[C:68](F)(F)[C:69]([OH:71])=O>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH2:13][N:12]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C:11]([CH2:25][CH2:68][C:69]([NH:38][OH:37])=[O:71])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=1

Participants

8

Reactant 6

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 4691350O-(tert-Butyldimethylsilyl)hydroxylamineHCID 10046528HCID 10046528, compound

Product 1

HCID 10070444HCID 10070444, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 40 mg (0.10 mmol) of acid 24-1 in DMF was added 18 mg (0.12 mmol) of O-(t-butyldimethylsilyl)hydroxylamine, 29 mg (0.15 mmol) of EDCI, 17 mg (0.13 mmol) HOAT, and 28 μL (0.20 mmol) of triethylamine. After stirring overnight at room temperature, ˜300 μL of trifluoroacetic acid was added and stirring was continued for 1 h. The reaction was partitioned between EtOAc and saturated NaHCO3, the organic phase was washed with brine, dried over MgSO4, and concentrated. The residue was purified by column chromatography on silica gel with MeOH/CHCl3 to provide 26-1 as a white solid. Data for 26-1: HRMS (ES) calc'd M+Na for C22H23F2N3O3: 438.1599. Found: 438.1618.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. customThe reaction was partitioned between EtOAc and saturated NaHCO3
  4. washthe organic phase was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel with MeOH/CHCl3

Sources & evidence

ORD record
ord-953ea6b34b6f43a8a9f859b9f3ac1726
Source dataset
uspto-grants-2007_06
Patent number
US07235580B2

Reaction notes

Loading…