Hydroxyamine hydrochloride → HCID 59384353, compound

HRID 2357076Notes

Reaction equation

HRID 2357076 reaction equation
CC1(C)[N:6](C(OC(C)(C)C)=O)[C@:5]([CH3:38])([C:14](=[O:37])[CH2:15][C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:20]([C:33]([F:36])([F:35])[F:34])[CH:19]=2)=O)[CH2:4][O:3]1.Cl.[NH2:41]O.C(O)(C(F)(F)F)=O.C(Cl)Cl>N1C=CC=CC=1>[NH2:6][C@@:5]([C:14]1[O:37][N:41]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[C:20]([C:33]([F:36])([F:35])[F:34])[CH:19]=2)[CH:15]=1)([CH3:38])[CH2:4][OH:3]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 21863450Trifluoroacetic acid methylene chlorideHCID 68455964HCID 68455964, compound

Product 1

HCID 59384353HCID 59384353, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The solution of (S)-tert-butyl 2,2,4-trimethyl-4-(3-(4-(octyloxy)-3-(trifluoromethyl)-phenyl)-3-oxo-propanoyl)oxazolidine-3-carboxylate (27 mg, 0.05 mmol, 1.0 equiv) and hydroxylamine hydrochloride (6.6 mg, 0.10 mmol, 2.0 equiv) in pyridine (0.5 mL) was stirred at 60° C. for 2 days. The reaction was condensed and the residue was treated with 20% TFA-DCM for 30 min. After removal of excess amount of TFA and DCM, the crude product was purified by prep. HPLC and afforded the title compound as mono-TFA salt (6.0 mg). MS (ESI, M+H+)=415.0; 1H NMR (400 MHz, CD3OD) δ 8.06 (s, 1H), 8.04 (d, 1H, J=9.6 Hz), 7.31 (d, 1H, J=9.6 Hz), 7.03 (s, 1H), 4.16 (t, 2H, J=6.0 Hz), 4.01, 3.83 (AB, 2H, J=12.0 Hz), 1.87-1.80 (m, 2H), 1.75 (s, 3H), 1.56-1.47 (m, 2H), 1.40-1.32 (m, 8H), 0.91 (t, 3H, J=7.2 Hz).

Workup

  1. customcondensed
  2. customAfter removal of excess amount of TFA and DCM
  3. customthe crude product was purified by prep

Sources & evidence

ORD record
ord-35f028d57951455f868a450c1bab0bf1
Source dataset
uspto-grants-2010_07
Patent number
US07759370B2

Reaction notes

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