Water → HCID 18738154, compound

HRID 1934376Notes

Reaction equation

HRID 1934376 reaction equation
Cl.[N:2]([CH2:5][C@H:6]([NH2:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N+:3]=[N-:4].C(N(CC)CC)C.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>ClCCl>[N:2]([CH2:5][C@H:6]([NH:12][C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N+:3]=[N-:4]

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 18734737HCID 18734737, compound

Product 1

HCID 18738154HCID 18738154, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 3 azido-2(S)-aminopropionate hydrochloride (0.3 g) in dichloromethane (3 ml) was added triethylamine (0.47 ml) and benzoyl chloride (0.2 ml) under stirring at 0° C. After stirring at ambient temperature for 2 hours, the mixture was poured into water and extracted with dichloromethane. The extract was washed with water, saturated aq. NaHCO3, water and brine, and dried over magnesium sulfate, and evaporated in vacuo. The residue was recrystallized from diethyl ether to give ethyl 3 azido-2(S)-(benzoylamino)propionate (0.35 g).

Workup

  1. stirringAfter stirring at ambient temperature for 2 hours
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with water, saturated aq. NaHCO3, water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-f573d30714ef4e27b2f74a1aee3d14bc
Source dataset
uspto-grants-2002_05
Patent number
US06384028B1

Reaction notes

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