Carbamic acid, [(1,1-dimethylethyl)carbonimidoyl]-, methyl ester → HCID 54535399, compound

HRID 374867Notes

Reaction equation

HRID 374867 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][C:13]1[C:18](=[O:19])[CH2:17][CH2:16][CH2:15][C:14]=1[CH2:20][C:21](O)=[O:22])=[CH:7]2.[CH3:24][O:25][C:26]([N:28]=C=NC(C)(C)C)=[O:27]>C1COCC1>[CH3:24][O:25][C:26](=[O:27])[NH:28][C:21](=[O:22])[CH2:20][C:14]1[CH2:15][CH2:16][CH2:17][C:18](=[O:19])[C:13]=1[CH2:12][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[Br:1])[CH:7]=1

Participants

4

Reactant 2

HCID 13166629Carbamic acid, [(1,1-dimethylethyl)carbonimidoyl]-, methyl esterHCID 15284123HCID 15284123, compound

Product 1

HCID 54535399HCID 54535399, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [2-(5-bromo-naphthalen-2-ylmethyl)-3-oxo-cyclohex-1-enyl]-acetic acid (1.1 g, 2.95 mmol), N-methoxycarbonyl-N'-tert-butylcarbodiimide (0.51 g, 3.25 mmol), and THF (20 mL) was refluxed for 4 hours. The volatiles were removed in vacuo and the residue was purified by flash chromatography on silica gel (eluting solvent hexane/EtOAc 2/1 ) to give a white solid (0.95 g, 76% yield, m.p. 128°-129° C.).

Workup

  1. temperaturewas refluxed for 4 hours
  2. customThe volatiles were removed in vacuo
  3. customthe residue was purified by flash chromatography on silica gel (eluting solvent hexane/EtOAc 2/1 )

Sources & evidence

ORD record
ord-4b8e9cac92ed4789b6641b7a350d905b
Source dataset
uspto-grants-1996_01
Patent number
US05482968

Reaction notes

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