Ethanolamine → HCID 67634939, compound

HRID 337381Notes

Reaction equation

HRID 337381 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:31][CH2:32][CH2:33][OH:34].C(=O)([O-])O.[Na+]>C(Cl)Cl.O>[OH:34][CH2:33][CH2:32][NH:31][C:14]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:18][CH:17]=1)=[O:16]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 8536054-(((tert-Butoxycarbonyl)amino)methyl)benzoic acid

Product 1

HCID 67634939HCID 67634939, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2.06 g (8.21 mmol) of 4-[(tert-butoxycarbonylamino)methyl]benzoic acid suspended in 40 mL of methylene chloride was mixed with 1.63 g (10.1 mmol) of 1,1′-carbonyldiimidazole at room temperature and stirred at room temperature for 1.5 hours. The reaction solution was further stirred with 1.8 mL (30 mmol) of 2-aminoethanol overnight, and after addition of 40 mL of saturated aqueous sodium hydrogen carbonate, 20 mL of water and 200 mL of methylene chloride, was allowed to separate. The organic layer was washed with 80 mL of 1 M hydrochloric acid, with 40 mL of saturated aqueous sodium hydrogen carbonate and with 20 mL of saturated aqueous sodium chloride twice, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the desired product (2.30 g, yield 95%).

Workup

  1. customto separate
  2. washThe organic layer was washed with 80 mL of 1 M hydrochloric acid, with 40 mL of saturated aqueous sodium hydrogen carbonate and with 20 mL of saturated aqueous sodium chloride twice
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-81a8792cc6ff4c44bac37c0473162863
Source dataset
uspto-grants-2014_11
Patent number
US08889732B2

Reaction notes

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