p-Toluenesulfonic acid → HCID 16659479, compound

HRID 990951Notes

Reaction equation

HRID 990951 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:11][C@H:12]([CH2:15][CH3:16])[CH2:13][OH:14].C(O[CH:20](O)[C:21]([F:24])([F:23])[F:22])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C@H:12]([CH2:15][CH3:16])[CH2:13][O:14][CH:20]1[C:21]([F:24])([F:23])[F:22]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9897Ethanol, 1-ethoxy-2,2,2-trifluoro-HCID 16659476HCID 16659476, compound

Product 1

HCID 16659479HCID 16659479, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

This compound was prepared according to General Method 19 (EXAMPLE 45) from (2R)-2-(2-fluoro-4-nitrophenyl)amino-1-butanol (1.6 g, 70 mmol), trifluoroacetaldehyde ethyl hemiacetal (4.9 g, 34 mmol) and p-toluenesulfonic acid (0.13 g, 0.68 mmol) in 70 mL anhydrous benzene to afford 1.8 g (85%) of (4R)-3-(2-fluoro-4-nitrophenyl)-4-ethyl-2-trifluoromethyloxazolidine, after flash chromatography (gradient elution, hexanes:ethyl acetate 90:10 to 50:50). Data for (4R)-3-(2-fluoro-4-nitrophenyl)-4-ethyl-2-trifluoromethyloxazolidine: 1H NMR (500 MHz, CDCl3) δ 8.01 (m, 1H), 7.98 (m, 1H), 6.95 (dd, J=8.8, 8.8, 1H), 5.68 (m, 1H), 4.30 (m, 1H), 4.08 (m, 1H), 3.92 (m, 1H), 2.00 (m, 1H), 1.67 (m, 1H), 0.97 (t, J=7.8, 3H).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-642b9dd72e294516956e60b50d98e878
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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