Acetic Acid → HCID 70873963, compound

HRID 2208756Notes

Reaction equation

HRID 2208756 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].O=[CH:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:20]([O:19][C:18]([NH:17][CH2:16][CH2:15][NH:1][C:2]1[C:3]([CH3:13])=[C:4]([CH:9]=[C:10]([Cl:12])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])=[O:24])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5003444Sodium cyanoborohydrideHCID 68295455Methyl 3-amino-5-chloro-2-methylbenzoate

Product 1

HCID 70873963HCID 70873963, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 3-amino-5-chloro-2-methylbenzoate (1 g, 4.6 mmol) and tert-butyl (2-oxoethyl)carbamate (1.4 g, 8.8 mmol) in methanol (10 mL), acetic acid (0.027 g, 4.6 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (0.352 g, 4.68 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford the desired product (0.62 g, 38%).

Workup

  1. customreaction
  2. customreaction
  3. stirringstirred overnight
  4. customOn completion, solvent was removed under reduced pressure and crude material
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-31b8ceeb5b2748c8a1712732615d53ca
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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