Ammonia → HCID 22987252, compound

HRID 2301004Notes

Reaction equation

HRID 2301004 reaction equation
[C:1]([NH2:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].F[B-](F)(F)F.[CH2:13]([O+](CC)CC)C.N.Cl.C[O:23][C:24](=[O:29])[C@H:25]([CH2:27]O)N.ClC(Cl)C>ClCCl>[C:2]([C:1]1[O:6][CH2:13][CH:27]([CH2:25][C:24]([OH:23])=[O:29])[N:7]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 63651,1-DichloroethaneHCID 12957TrimethylacetamideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 2723982Triethyloxonium tetrafluoroborate

Product 1

HCID 22987252HCID 22987252, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 g (29.6 mmol) of pivalic acid amide are stirred with 5.6 g (29.6 mmol) of triethyloxonium tetrafluoroborate in 50 ml of dichloromethane for 48 h. Ammonia is passed through the solution over a period of 3 h, the resulting residue is filtered off and the filtrate is concentrated in a rotary evaporator. 4.67 g (30 mmol) of L-serine methyl ester hydrochloride are added with 50 ml of dichloroethane, and the mixture is then heated at reflux for 8 h. Extraction with NaHCO3 solution and NH4Cl solution, drying over MgSO4 and purification by column chromatography (15×3 cm, pentane/diethyl ether 4:1) are carried out. Yield 1.34 g (24% of theory).

Workup

  1. filtrationthe resulting residue is filtered off
  2. concentrationthe filtrate is concentrated in a rotary evaporator
  3. temperaturethe mixture is then heated
  4. temperatureat reflux for 8 h
  5. extractionExtraction with NaHCO3 solution and NH4Cl solution
  6. dry with materialdrying over MgSO4 and purification by column chromatography (15×3 cm, pentane/diethyl ether 4:1)

Sources & evidence

ORD record
ord-2a45592384054758a470d9b4218c5735
Source dataset
uspto-grants-2002_12
Patent number
US06498256B2

Reaction notes

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