Ethanolamine → Tert-butyl 3-{[(benzyloxy)carbonyl](2-hydroxyethyl)amino}propanoate

HRID 655509Notes

Reaction equation

HRID 655509 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5]([O:9][C:10](=[O:13])[CH:11]=[CH2:12])([CH3:8])([CH3:7])[CH3:6].[CH2:14]([O:21][C:22](ON1C(=O)CCC1=O)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>O1CCCC1.O>[C:5]([O:9][C:10](=[O:13])[CH2:11][CH2:12][N:4]([C:22]([O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:23])[CH2:3][CH2:1][OH:2])([CH3:8])([CH3:7])[CH3:6]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 15458tert-Butyl acrylateHCID 83172Benzyl succinimido carbonate

Product 1

HCID 67074235Tert-butyl 3-{[(benzyloxy)carbonyl](2-hydroxyethyl)amino}propanoateYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

6.11 g (100 mmol) of ethanolamine were cooled (0° C.), treated with 14.52 ml (100 mmol) of ter-butyl-acrylate and stirred 15 min at this temperature. During warming up to room temperature the reaction started and was kept with cooling at 25-30° C. and then stirred 18 h at room temperature. The oil was dissolved in 500 ml of tetrahydrofuran and 500 ml of water, 27.42 (110 mmol) of N-(benzyloxycarbonyloxy)succinimide were added at 0° C. followed by 27.88 ml (200 mmol) of triethlamine. The reaction was stirred at room temperature over 3 h, then partitioned between 10% aq. potassium hydrogensulfate solution and diethyl ether (3×). The organic phases were washed with 10% aq. potassium hydrogensulfate solution, sat. aq. sodium hydrogencarbonate solution, 10% aq. sodium chloride solution, dried over Na2SO4 evaporated and purified by flash silica gel column (n-heptane/ethyl acetate 4:1 to 1:1) to yield 27.53 g (85%) of the title compound as light yellow oil. MS: 324.2 (MH+).

Workup

  1. temperaturewith cooling at 25-30° C.
  2. stirringstirred 18 h at room temperature
  3. stirringThe reaction was stirred at room temperature over 3 h
  4. custompartitioned between 10% aq. potassium hydrogensulfate solution and diethyl ether (3×)
  5. washThe organic phases were washed with 10% aq. potassium hydrogensulfate solution, sat. aq. sodium hydrogencarbonate solution, 10% aq. sodium chloride solution
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. custompurified by flash silica gel column (n-heptane/ethyl acetate 4:1 to 1:1)

Sources & evidence

ORD record
ord-7d5de77214794d828600a586cfb1f834
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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