4-Methylmorpholine → HCID 86640493, compound

HRID 561024Notes

Reaction equation

HRID 561024 reaction equation
ClC(OCC)=O.[C:7]([O:11][C:12]([NH:14][CH2:15][CH2:16][C:17]([OH:19])=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].CN1CCOCC1.[N-:27]=[N+:28]=[N-:29].[Na+]>C1COCC1.O.C(OCC)(=O)C>[C:7]([O:11][C:12](=[O:13])[NH:14][CH2:15][CH2:16][C:17]([N:27]=[N+:28]=[N-:29])=[O:19])([CH3:10])([CH3:9])[CH3:8]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanine

Product 1

HCID 86640493HCID 86640493, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-5 °C

Procedure

Add ethyl chloroformate (2.52 g, 23.25 mmol) dropwise to a solution of 3-tert-butoxycarbonylamino-propionic acid (4 g, 21.14 mmol) and 4-methyl morpholine (2.35 g, 23.25 mmol) in THF (60 mL) at −20° C. After 40 min, warm the suspension to −5° C. and add dropwise a solution of sodium azide (3.44 g, 52.85 mmol) in water (10 mL). After 10 min, dilute the mixture with ethyl acetate (60 mL) and wash with water, saturated aqueous sodium chloride, dry over MgSO4. After filtration, remove the organic solvent to afford the product as clear oil (4.3 g, 95%). 1H NMR (DMSO-d6) δ 6.91 (broad s, 1H), 3.18 (q, J=6.4 Hz, 2H), 2.51-2.48 (m, 2H), 1.37 (s, 9H).

Workup

  1. waitAfter 10 min
  2. washwash with water, saturated aqueous sodium chloride
  3. dry with materialdry over MgSO4
  4. filtrationAfter filtration
  5. customremove the organic solvent

Sources & evidence

ORD record
ord-823d93e6a3604959bca9908e36addea0
Source dataset
uspto-grants-2011_11
Patent number
US08063212B2

Reaction notes

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