Adipic Acid → HCID 58658626, compound

HRID 720953Notes

Reaction equation

HRID 720953 reaction equation
[CH3:1][C:2]([NH:4][CH:5]1[C:15]2[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]=2[C:13]2[C:8](=[CH:9][C:10]([O:25][CH3:26])=[C:11]([O:23][CH3:24])[C:12]=2[O:21][CH3:22])[CH2:7][CH2:6]1)=[O:3].[C:27](O)(=[O:35])[CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33].C(N(C(C)C)CC)(C)C>C(#N)C>[C:2]([NH:4][C@@H:5]1[C:15]2[CH:16]=[C:17]([O:20][C:27]([CH2:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=[O:33])=[O:35])[CH:18]=[CH:19][C:14]=2[C:13]2[C:12]([O:21][CH3:22])=[C:11]([O:23][CH3:24])[C:10]([O:25][CH3:26])=[CH:9][C:8]=2[CH2:7][CH2:6]1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 196Adipic AcidHCID 81531DiisopropylethylamineHCID 97865N-Acetylcolchicinol

Product 1

HCID 58658626HCID 58658626, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Acetyl-colchicinol (0.3 g; 0.84 mmol) was added under argon atmosphere to a solution of adipic acid (0.147 g; 1 mmol, O-(7-(azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.383 g; 1 mmol) and diisopropylethylamine (0.352 ml; 2 mmol) in acetonitrile (20 ml). The reaction mixture was stirred at ambient temperature overnight and evaporated to dryness. The residue was taken up in water (4 ml), the pH was adjusted to 6.5 with 0.1M hydrochloric acid. The solution was purified by preparative HPLC eluting with a 0–40% gradient of methanol/ammonium carbonate buffer (2 g/l pH7) to give 5-[{(5S)-5-(acetylamino)-9,10,11-trimethoxy-6,7-dihydro-5H-dibenzo[a,c]cyclohepten-3-yl}oxycarbonyl]pentanoic acid.

Workup

  1. customevaporated to dryness
  2. customThe solution was purified by preparative HPLC
  3. washeluting with a 0–40% gradient of methanol/ammonium carbonate buffer (2 g/l pH7)

Sources & evidence

ORD record
ord-f20d7d3b616443d58ab87357f0202c7b
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Reaction notes

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