Benzyloxycarbonylglycine → HCID 85923149, compound

HRID 1485121Notes

Reaction equation

HRID 1485121 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:39][Si:40]([CH3:45])([CH3:44])[CH2:41][CH2:42]O>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([O:15][CH2:42][CH2:41][Si:40]([CH3:45])([CH3:44])[CH3:39])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 14349BenzyloxycarbonylglycineHCID 180132-(Trimethylsilyl)ethanol2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 85923149HCID 85923149, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To a mixture of N-[(benzyloxy)carbonyl]glycine (5.33 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.86 g), 1-hydroxybenzotriazole monohydrate (4.68 g) and chloroform (51.0 mL), 2-(trimethylsilyl)ethanol (4.36 mL) was added and the mixture was stirred at room temperature for 8 hours. To the reaction mixture, 2-(trimethylsilyl)ethanol (3.00 mL), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.93 g) and 4-dimethylaminopyridine (312 mg) were added and the mixture was stirred at room temperature for 65 hours. After pouring the reaction mixture into a saturated aqueous solution of ammonium chloride, three extractions were conducted with ethyl acetate. The combined organic layers were washed with saturated brine and dried over anhydrous magnesium sulfate. After removing the desiccant by filtration, the filtrate was concentrated under reduced pressure and purified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-80:20) to give 2-(trimethylsilyl)ethyl N-[(benzyloxy)carbonyl]glycinate as a colorless oil (6.64 g).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 65 hours
  3. additionAfter pouring the reaction mixture
  4. extractioninto a saturated aqueous solution of ammonium chloride, three extractions
  5. washThe combined organic layers were washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter removing the
  8. filtrationdesiccant by filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. custompurified by silica gel column chromatography (n-hexane:ethyl acetate=95:5-80:20)

Sources & evidence

ORD record
ord-616297b7674345a58bfa9d9dda879dc0
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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