Acetic Anhydride → 2-Acetoxy-4-{4-[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-carbonyl]-2-cyclopentyl-phenoxysulfonyl}-benzoic Acid

HRID 1280935Notes

Reaction equation

HRID 1280935 reaction equation
[Br:1][C:2]1[CH:42]=[CH:41][CH:40]=[CH:39][C:3]=1[CH2:4][C:5]1[O:6][C:7]([CH3:38])=[C:8]([CH3:37])[C:9]=1[C:10]([C:12]1[CH:31]=[CH:30][C:15]([O:16][S:17]([C:20]2[CH:28]=[CH:27][C:23]([C:24]([OH:26])=[O:25])=[C:22]([OH:29])[CH:21]=2)(=[O:19])=[O:18])=[C:14]([CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:13]=1)=[O:11].[I-].[Mg+2].[I-].[C:46](OC(=O)C)(=[O:48])[CH3:47]>CCOCC>[C:46]([O:29][C:22]1[CH:21]=[C:20]([S:17]([O:16][C:15]2[CH:30]=[CH:31][C:12]([C:10]([C:9]3[C:8]([CH3:37])=[C:7]([CH3:38])[O:6][C:5]=3[CH2:4][C:3]3[CH:39]=[CH:40][CH:41]=[CH:42][C:2]=3[Br:1])=[O:11])=[CH:13][C:14]=2[CH:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)(=[O:19])=[O:18])[CH:28]=[CH:27][C:23]=1[C:24]([OH:26])=[O:25])(=[O:48])[CH3:47]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 5462737Magnesium diiodideHCID 101223524-{4-[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-carbonyl]-2-cyclopentyl-phenoxysulfonyl}-2-hydroxy-benzoic Acid

Product 1

HCID 101756482-Acetoxy-4-{4-[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-carbonyl]-2-cyclopentyl-phenoxysulfonyl}-benzoic AcidYield 25%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound was prepared according to the procedure in Example 22 using 4-{4-[2-(2-bromo-benzyl)-4,5-dimethyl-furan-3-carbonyl]-2-cyclopentyl-phenoxysulfonyl}-2-hydroxy-benzoic acid (0.318 g, 0.487 mmol), magnesium iodide (0.132 g, 0.475 mmol) and acetic anhydride (3.8 mL) in ether. Purification on 2% H3PO4/MeOH treated silica gel, eluting with a 30% EtOAc/pet ether gave 0.083 g (25%) of the title compound as a solid, mp 79° C. 1H NMR (DMSO-d6) δ 1.27-1.33 (m, 2H), 1.51-1.54 (m, 2H), 1.63-1.73 (m, 4H), 1.79 (s, 3H), 2.17 (s, 3H), 2.24 (s, 3H), 2.93 (quintet, 1H), 3.91 (s, 2H), 7.13-7.17 (m, 2H), 7.21 (d, 1H), 7.30 (dt, 1H), 7.51 (dd, 1H), 7.55 (dd, 1H), 7.60 (d, 1H), 7.85 (d, 1H), 7.90 (dd, 1H), 8.14 (d, 1H)13.8 (br s, 1H). mass spectrum (−ESI) m/z 693/695 (M−H). Anal. Calcd. for C34H31BrO9S: C, 58.71; H, 4.49; N, 0.00. Found: C, 58.04; H, 4.52; N, 0.04.

Workup

  1. customThe title compound was prepared
  2. customPurification on 2% H3PO4/MeOH
  3. additiontreated silica gel
  4. washeluting with a 30% EtOAc/pet ether

Sources & evidence

ORD record
ord-4031b82442b54be08e6bfefeadc4bab9
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

Loading…