Water → methyl(S)-3-tert-butoxycarbonylamino-2-morpholin-4-ylpropanoate

HRID 1620387Notes

Reaction equation

HRID 1620387 reaction equation
Cl[CH2:2][CH2:3][O:4][CH2:5][CH2:6]Cl.[NH2:8][C@@H:9]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10]([O:12][CH3:13])=[O:11].O>C(N(C(C)C)CC)(C)C>[C:19]([O:18][C:16]([NH:15][CH2:14][C@H:9]([N:8]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)[C:10]([O:12][CH3:13])=[O:11])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 8115Bis(2-chloroethyl) etherHCID 7021143Methyl 3-((tert-butoxycarbonyl)amino)-L-alaninate

Product 1

HCID 67056346methyl(S)-3-tert-butoxycarbonylamino-2-morpholin-4-ylpropanoateYield 24.3%

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
127 °C

Procedure

2.8 g (20 mmol) of 1-chloro-2-(2-chloroethoxy)ethane are added to a solution of 5 g (20 mmol) of commercial methyl(S)-2-amino-3-tert-butoxycarbonylaminopropanoate in 65 ml of diisopropylethylamine. The reaction mixture is stirred at 127° C. for 18 h. After the addition of water, the reaction medium is extracted with ethyl acetate. The organic phases are combined, dried over sodium sulfate, filtered and evaporated. The residue obtained is purified by chromatography on silica gel, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 1.4 g (24%) of methyl(S)-3-tert-butoxycarbonylamino-2-morpholin-4-ylpropanoate are obtained in the form of an oil.

Workup

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on silica gel, elution

Sources & evidence

ORD record
ord-1fab35d85d4e444faac3bb95a0ba71ef
Source dataset
uspto-grants-2014_07
Patent number
US08772478B2

Reaction notes

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