Acetic Anhydride → 4-[3-{6-[3-(4-Acetyl-piperazine-1-carbonyl)-5-benzo[1,3]dioxol-5-yl-phenoxy]-hexyl}-2-(2-carboxy-ethyl)-phenoxy]-butyric Acid

HRID 1670078Notes

Reaction equation

HRID 1670078 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:11]=[C:12]([CH:38]=[C:39]([C:41]([N:43]4[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]4)=[O:42])[CH:40]=3)[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]3[C:21]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[C:22]([CH:30]=[CH:31][CH:32]=3)[O:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:9][C:4]=2[O:3][CH2:2]1.[C:49](OC(=O)C)(=[O:51])[CH3:50].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:49]([N:46]1[CH2:45][CH2:44][N:43]([C:41]([C:39]2[CH:38]=[C:12]([CH:11]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)[CH:40]=2)[O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[C:21]([CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[C:22]([CH:30]=[CH:31][CH:32]=2)[O:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:42])[CH2:48][CH2:47]1)(=[O:51])[CH3:50]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 426303214-[3-{6-[3-Benzo[1,3]dioxol-5-yl-5-(piperazine-1-carbonyl)-phenoxy]-hexyl}-2-(2-carboxy-ethyl)-phenoxy]-butyric acid

Product 1

HCID 673390604-[3-{6-[3-(4-Acetyl-piperazine-1-carbonyl)-5-benzo[1,3]dioxol-5-yl-phenoxy]-hexyl}-2-(2-carboxy-ethyl)-phenoxy]-butyric Acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[3-{6-[3-Benzo[1,3]dioxol-5-yl-5-(piperazine-1-carbonyl)-phenoxy]-hexyl}-2-(2-carboxy-ethyl)-phenoxy]-butyric acid (0.29 mmol), acetic anhydride (1.2 eq.), triethylamine (3 eq.) were combined in dichloromethane (2 mL) and stirred overnight. Then the reaction mixture was diluted with ethyl acetate, washed with water and dried over anhydrous sodium sulfate. The organic extract was concentrated under reduced pressure and purified by reverse-phase HPLC to yield the title compound.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. extractionThe organic extract
  4. concentrationwas concentrated under reduced pressure
  5. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-56601493fce84ec584e5a8823c8abad4
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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