Triethylamine → HCID 69885957, compound

HRID 1245300Notes

Reaction equation

HRID 1245300 reaction equation
C(OC([N:8]1[C:13](=[O:14])[CH:12]2[CH:10]([CH:11]2[C:15]([O-:17])=[O:16])[CH:9]1[C:18]([O-:20])=[O:19])=O)(C)(C)C.Cl.[NH2:22][CH2:23][C:24]([O:26]CC)=[O:25].CCN(CC)CC>C1COCC1.[C-]#N.[K+]>[C:15]([CH:11]1[CH:12]([C:13]([NH:8][CH2:9][C:18]([OH:20])=[O:19])=[O:14])[CH:10]1[CH:23]([C:24]([OH:26])=[O:25])[NH2:22])([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 21911181HCID 21911181, compound

Product 1

HCID 69885957HCID 69885957, compoundYield 164.2%

Reagents, catalysts & solvents 2

HCID 9032Potassium CyanideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (1SR, 2SR, 5RS, 6RS) 3-tert -butoxycarbonyl-4-oxo-3-azabicyclo[3.1.0]hexane-2,6-dicarboxylate (190 mg, 0.55 mmol) in dry THF (3.5 mL) under argon was added ethyl glycinate hydrochloride (466 mg, 3.34 mmol), potassium cyanide (1.7 mg, 0.02 mmol) and Et3N (0.44 mL, 3.34 mmol). After stirring overnight in an ultrasonic bath, the solvent was removed under reduced pressure. The residue was directly purified by flash chromatography (hexane/ethyl acetate 1/1) to give 235 mg of the desired compound (95% yield).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was directly purified by flash chromatography (hexane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-2a0e5b235b1d4b71a46db0367dffcddf
Source dataset
uspto-grants-2006_10
Patent number
US07125871B2

Reaction notes

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