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

HRID 1280933Notes

Reaction equation

HRID 1280933 reaction equation
[CH2:1]([C:8]1[S:9][C:10]([CH3:41])=[C:11]([CH3:40])[C:12]=1[C:13]([C:15]1[CH:34]=[CH:33][C:18]([O:19][S:20]([C:23]2[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[C:25]([OH:32])[CH:24]=2)(=[O:22])=[O:21])=[C:17]([CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:16]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Mg+2].[I-].[C:45](OC(=O)C)(=[O:47])[CH3:46]>CCOCC>[C:45]([O:32][C:25]1[CH:24]=[C:23]([S:20]([O:19][C:18]2[CH:33]=[CH:34][C:15]([C:13]([C:12]3[C:11]([CH3:40])=[C:10]([CH3:41])[S:9][C:8]=3[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:14])=[CH:16][C:17]=2[CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)(=[O:22])=[O:21])[CH:31]=[CH:30][C:26]=1[C:27]([OH:29])=[O:28])(=[O:47])[CH3:46]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 5462737Magnesium diiodideHCID 101212614-[4-(2-Benzyl-4,5-dimethyl-thiophene-3-carbonyl)-2-cyclopentyl-phenoxysulfonyl]-2-hydroxy-benzoic Acid

Product 1

HCID 102828142-Acetoxy-4-[4-(2-benzyl-4,5-dimethyl-thiophene-3-carbonyl)-2-cyclopentyl-phenoxysulfonyl]-benzoic AcidYield 51%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound was prepared according to the procedure in Example 22 using 4-[4-(2-benzyl-4,5-dimethyl-thiophene-3-carbonyl)-2-cyclopentyl-phenoxysulfonyl]-2-hydroxy-benzoic acid (0.233 g, 0.394 mmol), magnesium iodide (0.110 g, 0.394 mmol) and acetic anhydride (3.3 mL) in ether. Purification on 2% H3PO4/MeOH treated silica gel, eluting with 18% EtOAc/pet ether followed by a second chromatography on 2% H3PO4/MeOH treated silica gel, eluting with 5% CH3CN/CH2Cl2 gave 0.128 g (51%) of the title compound as a white solid, mp 94-96° C. 1H NMR (DMSO-d6) δ 1.24-1.33 (m, 2H), 1.52-1.57 (m, 2H), 1.61-1.76 (m, 4H), 1.79 (s, 3H), 2.23 (s, 3H), 2.26 (s, 3H), 2.94 (quintet, 1H), 3.85 (s, 2H), 6.99-7.01 (m, 2H), 7.13 (m, 4H), 7.52 (dd, 1H), 7.59 (d, 1H), 7.84 (d, 1H), 7.90 (dd, 1H), 8.14 (d, 1H), 13.8 (br s, 1H). mass spectrum (−ESI) m/z 631 (M−H). Anal. Calcd. for C34H32O8S20.2H2O: C, 64.17; H, 5.13; N, 0.00. Found: C, 64.06; H, 4.98; N, 0.04.

Workup

  1. customThe title compound was prepared
  2. customPurification on 2% H3PO4/MeOH
  3. additiontreated silica gel
  4. washeluting with 18% EtOAc/pet ether
  5. additiontreated silica gel
  6. washeluting with 5% CH3CN/CH2Cl2

Sources & evidence

ORD record
ord-599976a5f41540a4abfbdb37d1974462
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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