Methyl 3-Hydroxyphenylacetate → HCID 11634491, compound

HRID 2422030Notes

Reaction equation

HRID 2422030 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.CC1C=CC(S(O[CH2:24][CH2:25][CH2:26][NH:27][C:28]2[C:29](=[O:45])[N:30]([C:41]([CH3:44])([CH3:43])[CH3:42])[S:31](=[O:40])(=[O:39])[C:32]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=O)=O)=CC=1>>[C:41]([N:30]1[C:29](=[O:45])[C:28]([NH:27][CH2:26][CH2:25][CH2:24][O:1][C:2]2[CH:3]=[C:4]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=2)=[C:32]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[S:31]1(=[O:39])=[O:40])([CH3:42])([CH3:43])[CH3:44]

Participants

3

Reactant 2

HCID 39129Methyl 3-HydroxyphenylacetateHCID 866258673-[(2-Tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate

Product 1

HCID 11634491HCID 11634491, compoundYield 66%

Procedure

The title compound was prepared as described for Example 12 from methyl (3-hydroxyphenyl)acetate and 3-[(2-tert-butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]propyl 4-methylbenzenesulfonate. The reaction mixture was evaporated and the residue was purified by silica gel column chromatography (Horizons Biotage) using 20-40% EtOAc in petroleum ether 40-60° C. as eluent. The product containing fractions were evaporated and the residue was dissolved in EtOAc, washed with aqueous K2CO3 (2M) and evaporated give the title compound (0.097 g, 66%). 1H NMR (500 MHz CDCl3): δ 7.55-7.48 (m, 2H), 7.46-7.40 (m, 3H), 7.26 (t, 1H), 6.90 (dd, 1H), 6.82-6.78 (m, 2H), 5.76 (t, 1H), 3.90 (t, 2H), 3.72 (s, 3H), 3.61 (s, 2H), 3.14-3.06 (m, 2H), 1.90-1.80 (m, 2H), 1.75 (s, 9H); 13C NMR (125 MHz CDCl3): δ 172.1, 159.8, 158.7, 135.7, 135.3, 131.8, 129.9, 129.8, 128.8, 125.3, 122.3, 115.5, 113.4, 107.2, 65.9, 61.7, 52.3, 42.4, 41.4, 29.0, 27.8; Mass Spectrum: M+H+ 487.

Workup

  1. customThe title compound was prepared
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by silica gel column chromatography (Horizons Biotage)
  4. custom20-40% EtOAc in petroleum ether 40-60° C.
  5. additionThe product containing fractions
  6. customwere evaporated
  7. dissolutionthe residue was dissolved in EtOAc
  8. washwashed with aqueous K2CO3 (2M)
  9. customevaporated

Sources & evidence

ORD record
ord-ffe24a3f38604eaead0507ba54857495
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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