Ethyl chloroformate → HCID 86761195, compound

HRID 1160240Notes

Reaction equation

HRID 1160240 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][N:10]=[CH:11][C:12]2[CH:13]=[C:14](/[CH:18]=[CH:19]/[C:20]([NH:22][O:23]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[O:21])[CH:15]=[CH:16][CH:17]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:43]C(OCC)=O>C1COCC1>[ClH:43].[OH:23][NH:22][C:20](=[O:21])/[CH:19]=[CH:18]/[C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH:11]=[N:10][O:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:13]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 86761197HCID 86761197, compound

Product 1

HCID 86761195HCID 86761195, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound ST3576 was obtained (0.931 mg, 98% yield) after acid hydrolysis of (2E)-3-{3-[(2-Morpholin-4-yl-ethoxyimino)-methyl]-phenyl}-N-trityloxy-acrylamide obtained (1.500 g, 2.67 mmol, 65% yield) by reaction of intermediate C (1.400 g, 4.12 mmol) with ethyl chloroformate (472 μL, 4.94 mmol) and TEA (746 μL, 5.35 mmol) in 5 mL of anhydrous THF (according to procedure described in Mai A., Pezzi R. et all. J. Med. Chem. 2005, 48, 3344 and in Mai A., Pezzi R. et all. J. Med. Chem. 2003, 46, 4826).

Workup

  1. customCompound ST3576 was obtained (0.931 mg, 98% yield)
  2. customobtained (1.500 g, 2.67 mmol, 65% yield)

Sources & evidence

ORD record
ord-572d94140c3d400d85745029177f5c0e
Source dataset
uspto-grants-2010_10
Patent number
US07816386B2

Reaction notes

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