Acetic Acid → HCID 70872341, compound

HRID 1530226Notes

Reaction equation

HRID 1530226 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([Br:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:14]([O:18][C:19](=[O:28])[NH:20][CH:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)([CH3:17])([CH3:16])[CH3:15].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[Br:12][C:10]1[CH:11]=[C:2]([NH:1][CH:24]2[CH2:23][CH2:22][CH:21]([NH:20][C:19]([O:18][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:28])[CH2:26][CH2:25]2)[C:3]([CH3:13])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 5003444Sodium cyanoborohydrideHCID 24729181Methyl 3-Amino-5-bromo-2-methylbenzoate

Product 1

HCID 70872341HCID 70872341, compoundYield 44.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-amino-5-bromo-2-methylbenzoate (5 g, 20.57 mmol) and tert-butyl(4-oxocyclohexyl)carbamate (5.6 g, 26.7 mmol) in methanol (50 mL) was added acetic acid (1.2 g, 20.57 mmol) and the reaction mixture stirred at room temperature for 8 h. Then sodium cyanoborohydride (1.6 g, 26.74 mmol) was added at 0° C. and the reaction stirred overnight. On completion, solvent was removed under reduced pressure and the crude material was purified by column chromatography twice eluting with ethyl acetate: hexane to afford methyl 5-bromo-3-((4-((tert-butoxycarbonyl)-amino)-cyclohexyl)-amino)-2-methylbenzoate 4 g (44%) of non-polar isomer (cis isomer, contaminated with starting) and 3 g (33%) of pure polar isomer (trans isomer).

Workup

  1. stirringthe reaction stirred overnight
  2. customOn completion, solvent was removed under reduced pressure
  3. customthe crude material was purified by column chromatography
  4. washtwice eluting with ethyl acetate

Sources & evidence

ORD record
ord-fafde41663c14ba6a5a3f978a4ce8851
Source dataset
uspto-grants-2015_07
Patent number
US09090562B2

Reaction notes

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