4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-[4-(4,5-Dimethyl-2-naphthalen-2-ylmethyl-furan-3-carbonyl)-2,6-diisopropyl-phenoxysulfonyl]-2-hydroxy-benzoic Acid

HRID 1871304Notes

Reaction equation

HRID 1871304 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][C:12]1[O:13][C:14]([CH3:33])=[C:15]([CH3:32])[C:16]=1[C:17]([C:19]1[CH:24]=[C:23]([CH:25]([CH3:27])[CH3:26])[C:22]([OH:28])=[C:21]([CH:29]([CH3:31])[CH3:30])[CH:20]=1)=[O:18].Cl[S:35]([C:38]1[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[C:40]([OH:47])[CH:39]=1)(=[O:37])=[O:36]>>[CH3:32][C:15]1[C:16]([C:17]([C:19]2[CH:20]=[C:21]([CH:29]([CH3:31])[CH3:30])[C:22]([O:28][S:35]([C:38]3[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[C:40]([OH:47])[CH:39]=3)(=[O:37])=[O:36])=[C:23]([CH:25]([CH3:26])[CH3:27])[CH:24]=2)=[O:18])=[C:12]([CH2:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)[O:13][C:14]=1[CH3:33]

Participants

3

Reactant 2

HCID 146685314-(Chlorosulfonyl)-2-hydroxybenzoic acidHCID 23445650(2-Naphthalen-2-ylmethyl-4,5-dimethyl-furan-3-yl)-(3,5-diisopropyl-4-hydroxy-phenyl)-methanone

Product 1

HCID 102331144-[4-(4,5-Dimethyl-2-naphthalen-2-ylmethyl-furan-3-carbonyl)-2,6-diisopropyl-phenoxysulfonyl]-2-hydroxy-benzoic AcidYield 55%

Procedure

The title compound was prepared according to the procedure in Example 4 using (2-naphthalen-2-ylmethyl-4,5-dimethyl-furan-3-yl)-(3,5-diisopropyl-4-hydroxy-phenyl)-methanone (0.300 g, 0.681 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.209 g, 0.885 mmol). Purification on Dynamax C18 (80% CH3CN/H2O) gave 0.240 g (55%) of the title compound as a yellow solid, mp 130-135° C. 1H NMR (DMSO-d6) δ 1.03 (d, 12 H), 1.83 (s, 3 H), 2.20 (s, 3 H), 3.09 (septet, 2 H), 4.01 (s, 2 H), 7.18 (d, 1 H), 7.43-7.48 (m, 5 H), 7.51 (s, 2 H), 7.77-7.79 (m, 2 H), 7.82-7.86 (m, 1 H), 8.05 (d, 1 H). IR (KBr) 3400, 2950, 1700, 1375 and 1190 cm-1. mass spectrum (-ESI) m/z 639 (M-H). Anal. Calcd. for C37H36O8S: C, 69.36; H, 5.66; N, 0.00. Found: C, 69.04; H, 5.77; N, 0.04.

Workup

  1. customThe title compound was prepared
  2. customPurification on Dynamax C18 (80% CH3CN/H2O)

Sources & evidence

ORD record
ord-ed2a1856fd0e4b56a3959884f13807b8
Source dataset
uspto-grants-2000_08
Patent number
US06103708

Reaction notes

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