Ethanolamine → HCID 59398197, compound

HRID 39817Notes

Reaction equation

HRID 39817 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:33][C:34]1[CH:43]=[CH:42][C:37]2[O:38][CH2:39][CH2:40][O:41][C:36]=2[CH:35]=1)[CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=3)[C:20]([C:29]([OH:31])=O)=[CH:19][C:18]2=[O:32])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)OCC.[NH2:50][CH2:51][CH2:52][OH:53].C(OC(C)C)(C)C>C(OCC)C.O.C(OCC)(=O)C.C(N(CC)CC)C.O1CCCC1>[O:38]1[C:37]2[CH:42]=[CH:43][C:34]([CH2:33][N:8]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][N:17]4[C:26]5[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH3:28])[CH:25]=5)[C:20]([C:29]([NH:50][CH2:51][CH2:52][OH:53])=[O:31])=[CH:19][C:18]4=[O:32])[CH2:13][CH2:14]3)[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[CH:35][C:36]=2[O:41][CH2:40][CH2:39]1

Participants

10

Reactant 4

HCID 700Ethanolamine3×HCID 7914Diisopropyl EtherHCID 10928Ethyl chloroformateHCID 593981451-(2-(4-((Tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylic acid

Product 1

HCID 59398197HCID 59398197, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3.0 mL of tetrahydrofuran suspension containing 0.15 g of 1-(2-(4-((tert-butoxycarbonyl)(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)amino)piperidin-1-yl)ethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylic acid, 39 μL of triethylamine was added at room temperature, 25 μL of ethyl chlorocarbonate was added dropwise under ice-cooling, and the reaction mixture was stirred at the same temperature for 2 hours. Then, 15 μL of 2-aminoethanol was added dropwise. After stirred at the same temperature for 3 hours, 15 μL of 2-aminoethanol was added dropwise and stirred for 1.5 hours. Further, 15 μL of 2-aminoethanol was added dropwise and stirred at room temperature for 40 min. To the reaction mixture, ethyl acetate and water were added, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and extracts were combined, washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. To the residue thus obtained, diethyl ether and diisopropyl ether were added, and the resulting solid was filtered to give 84 mg of tert-butyl (2,3-dihydro-1,4-benzodioxin-6-ylmethyl)(1-(2-(4-(((2-hydroxyethyl)amino)carbonyl)-7-methoxy-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a slight yellow solid.

Workup

  1. additionwas added at room temperature
  2. temperaturecooling
  3. stirringAfter stirred at the same temperature for 3 hours
  4. stirringstirred for 1.5 hours
  5. stirringstirred at room temperature for 40 min
  6. customthe organic layer was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washwashed sequentially with water and aqueous saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customTo the residue thus obtained
  12. filtrationthe resulting solid was filtered

Sources & evidence

ORD record
ord-d3fbdc3564384423a4b5e03b444df988
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

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