2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → Ethyl (N-{2-[(tert-butoxy)carbonylamino]acetylamino}carbamoyl)formate

HRID 2175412Notes

Reaction equation

HRID 2175412 reaction equation
[NH:1]([C:3](=[O:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[NH2:2].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.[C:28]([O:32][C:33]([NH:35][CH2:36][C:37](O)=[O:38])=[O:34])([CH3:31])([CH3:30])[CH3:29]>ClCCl>[C:28]([O:32][C:33]([NH:35][CH2:36][C:37]([NH:2][NH:1][C:3](=[O:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:38])=[O:34])([CH3:31])([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 2786935Ethyl 2-hydrazinyl-2-oxoacetate

Product 1

HCID 10108216Ethyl (N-{2-[(tert-butoxy)carbonylamino]acetylamino}carbamoyl)formateYield 85.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-hydrazinyl-2-oxoacetate (9-2) (0.516 g, 3.91 mmol) in dichloromethane (14 mL) was added EEDQ (0.78 g, 3.175 mmol) at room temperature and it was stirred for 15 min. Then 2-(tert-butoxycarbonylamino)acetic acid (9-3) (0.55 g, 3.175 mmol) was added. The mixture was stirred at room temperature for overnight. Solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel with gradient eluant (PE/EA=3/1 to 1/1). The product was obtained as a white solid (0.787 g, 85%). 1H NMR (400 MHz, CDCl3) δ 9.35 (s, 1H), 8.99 (s, 1H), 5.19 (s, 1H), 4.40 (dd, J=21.7, 7.2 Hz, 2H), 3.93 (d, J=6.1 Hz, 2H), 1.57-1.32 (m, 12H); LRMS (ESI) calculated M+Na for C11H19N3NaO6: 312.2. Found: 312.1.

Workup

  1. stirringThe mixture was stirred at room temperature for overnight
  2. customSolvent was removed under reduced pressure
  3. customthe residue was purified by chromatography on silica gel with gradient eluant (PE/EA=3/1 to 1/1)

Sources & evidence

ORD record
ord-8e467f788d9642fcad7ca27cf84276d2
Source dataset
uspto-grants-2015_06
Patent number
US09062059B2

Reaction notes

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