Trifluoroacetic acid → HCID 86699885, compound

HRID 1502222Notes

Reaction equation

HRID 1502222 reaction equation
C([NH:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][Br:16])(OC(C)(C)C)=O.[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20]>ClCCl>[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20].[Br:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][O:9][NH2:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86699887HCID 86699887, compound

Product 1

HCID 86699885HCID 86699885, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of N-Boc-O-(6-bromohexyl)hydroxylamine (954 mg, 3.22 mmol) in dichloromethane (16 mL) at 0° C. was added trifluoroacetic acid (8.0 mL). Stirring continued for 1 h at 0° C. (Gilmore, J. M.; Scheck, R. A.; Esser-Kahn, A. P.; Joshi, N. S.; Francis, M. B. Angew. Chem. Int. Ed. 2006, 45, 5307.) The volatile compounds were removed under reduced pressure and the excess acid was removed by azeotroping with toluene (3×20 mL). O-(6-bromohexyl)hydroxylamine trifluoroacetate salt (1b) was obtained as a clear oil (998 mg, quant.), which was carried on without further purification. 1H-NMR (CDCl3, 300 MHz): δ 10.41 (broad s, 3H), 4.05 (broad t, J=6.2 Hz, 2H), 3.4 (t, J=7.0 Hz, 2H), 1.85 (pent, J=6.7 Hz, 2H), 1.68 (broad pent, J=6.3 Hz, 2H), 1.51-1.33 (m, 4H). 13C-NMR (CDCl3, 75 MHz): δ 33.7, 32.6, 27.8, 27.6, 24.2. HRESI-MS calcd for C6H15BrON [M+H]+ 196.0332. found 196.0332.

Workup

  1. custom) The volatile compounds were removed under reduced pressure
  2. customthe excess acid was removed
  3. customby azeotroping with toluene (3×20 mL)

Sources & evidence

ORD record
ord-d1cafa7b83574659b595686092a80fc1
Source dataset
uspto-grants-2015_12
Patent number
US09206271B2

Reaction notes

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