Pyridine → HCID 86696308, compound

HRID 882371Notes

Reaction equation

HRID 882371 reaction equation
[NH2:1][CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].Cl.NCC(OCC1C=CC=CC=1)=O.C(=O)(O)[O-].[Na+].N1C=CC=CC=1.Cl[C:38]([O:40][CH:41]([Cl:43])[CH3:42])=[O:39]>C(Cl)Cl.O>[Cl:43][CH:41]([O:40][C:38]([NH:1][CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4])=[O:39])[CH3:42]

Participants

8

Reactant 5

HCID 1049PyridineHCID 409140Benzyl glycinate2×HCID 516892Sodium BicarbonateHCID 5213051-Chloroethyl chloroformateHCID 11701227Benzyl 2-aminoacetate hydrochloride

Product 1

HCID 86696308HCID 86696308, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Benzyl 2-aminoacetate was generated from a treatment of benzyl 2-aminoacetate hydrochloride (Aldrich) in methylene chloride with aqueous sodium bicarbonate solution followed by water wash. To a cooled solution of benzyl 2-aminoacetate (1.837 g, 11.1 mmol) and pyridine (1.1 g, 1.1 mL, 13.9 mmol) in methylene chloride (17 mL) at −78° C., was added slowly 1-chloroethyl chloroformate (Aldrich, 1.67 g, 11.7 mmol) over ˜10 min. The reaction mixture was allowed to stir at −78° C. for 3 h, giving a white precipitate. This cold reaction mixture was filtered to remove the solid and the filtrate was concentrated to dryness, giving the crude benzyl 2-((1-chloroethoxy)carbonylamino)acetate which was used for the next step without further purification.

Workup

  1. washwash
  2. customgiving a white precipitate
  3. customThis cold reaction mixture
  4. filtrationwas filtered
  5. customto remove the solid
  6. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-f86db14a0f7547e3a6936716e2e6f02b
Source dataset
uspto-grants-2015_03
Patent number
US08993614B2

Reaction notes

Loading…