p-Toluenesulfonic acid → HCID 902831, compound

HRID 2263653Notes

Reaction equation

HRID 2263653 reaction equation
[CH:1]1(/[CH:7]=[C:8](\[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[OH:24])=[O:17])/C(OC(C)(C)C)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>NC(N)=S.C1(C)C=CC=CC=1>[CH:1]1([C@H:7]2[CH2:8][C:16](=[O:17])[C:18]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[O:24]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 16125893HCID 16125893, compound

Product 1

HCID 902831HCID 902831, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 2723790ThioureaCatalystHCID 1140TolueneSolvent

Procedure

Prepared according to general procedure using (E)-tert-butyl 3-cyclohexyl-2-(2-hydroxyphenylcarbonyl)prop-2-enoate (66 mg, 0.20 mmol), thiourea catalyst III (14 mg, 0.020 mmol) in 2.0 mL toluene for 5 d at −25° C. and p-toluenesulfonic acid (19 mg, 0.10 mmol) for 4 h. Purification via column chromatography with 10% EtOAc/hexanes afforded 30.0 mg (65%) of 16 as a white solid in 80% ee. [α]D: −53.0 (EtOH, c=0.5). Analytical data for 16: IR (film) 2928.8, 1689.6, 1608.8, 1467.1, 1310.1, 1229.6 cm−1; 1H NMR (500 MHz, CDCl3) δ 7.87 (d, J=7.3 Hz, 1H), 7.47 (t, J=7.1 Hz, 1H), 7.01-6.97 (m, 2H), 4.23-4.19 (m, 1H), 2.77-2.65 (m, 2H), 2.01-1.99 (m, 1H), 1.84-1.72 (m, 5H), 1.35-1.11 (m, 5H); 13C NMR (125 MHz, CDCl3) δ 193.4, 162.1, 136.1, 127.1, 121.2 (x2), 118.1, 82.2, 42.0, 40.4, 28.5, 28.4, 26.5, 26.15, 26.09; LRMS (electrospray): Exact mass calcd for C15H18O2 [M]+, 230.13. Found [M+1], 231.7.

Workup

  1. customPrepared
  2. customfor 5 d
  3. customat −25° C.
  4. customPurification via column chromatography with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-08cf8610fc1943149c37c244e559ef48
Source dataset
uspto-grants-2010_12
Patent number
US07851640B2

Reaction notes

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