Triethylamine → (4-Methylamino-3-nitro-benzoylamino)-acetic acid tert-butyl ester

HRID 411050Notes

Reaction equation

HRID 411050 reaction equation
[CH3:1][NH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[C:15]([O:19][C:20](=[O:23])[CH2:21][NH2:22])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:15]([O:19][C:20](=[O:23])[CH2:21][NH:22][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][C:3]([NH:2][CH3:1])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 151417Glycine tert-butyl esterHCID 516892Sodium BicarbonateHCID 179464494-(Methylamino)-3-nitrobenzoyl chloride

Product 1

HCID 67332520(4-Methylamino-3-nitro-benzoylamino)-acetic acid tert-butyl esterYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(4-Methylamino-3-nitro-benzoylamino)-acetic acid tert-butyl ester (1.2 g) was prepared starting from 4-methylamino-3-nitro-benzoyl chloride (1 g), amino-acetic acid tert-butyl ester (721 mg), triethylamine (1.4 mL) in DCM (10 mL). The reaction was stirred at 0° C. for 1 h. The reaction was added to DCM (50 mL) and saturated sodium bicarbonate solution (50 mL). The phases were separated, and the aqueous phase was extracted twice with DCM. The combined organics were dried over sodium sulfate and then filtered. The solvent was evaporated and crude compound was purified by flash chromatography using DCM:methanol gradient.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted twice with DCM
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customcrude compound was purified by flash chromatography

Sources & evidence

ORD record
ord-7d412386c4344dfcac67f98674e7fd98
Source dataset
uspto-grants-2014_06
Patent number
US08759535B2

Reaction notes

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