4-Nitrobenzoyl chloride → tert-butyl 2-(N-(4-cyanobenzyl)-4-nitrobenzamido)acetate

HRID 923597Notes

Reaction equation

HRID 923597 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH2:7][NH:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:5][CH:4]=1)#[N:2].[N+:19]([C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1)([O-:21])=[O:20]>C(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[C:26](=[O:27])[C:25]2[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:30][CH:29]=2)=[CH:17][CH:18]=1)#[N:2]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 18000198tert-Butyl (4-cyanobenzyl)glycinate

Product 1

HCID 71076902tert-butyl 2-(N-(4-cyanobenzyl)-4-nitrobenzamido)acetateYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Prepared using General Procedure 7: To a stirred solution of tert-butyl 2-((4-cyanobenzyl)amino)acetate (14.7 g, 47.7 mmol) INT-31 in DCM (150 mL) stirring in a 0° C. in an ice bath was added TEA (9.98 mL, 71.6 mmol) followed by 4-nitrobenzoyl chloride. The reaction mixture was allowed to warm to room temperature over 1.5 h. The reaction mixture was diluted with DCM (300 mL) and washed with NaHCO3 (2×200 mL). The organics were dried over dried over MgSO4 and concentrated in vacuo. The crude product was purified by chromatography (MeOH/DCM) followed by evaporation from hexanes to provide 11.5 g (61%) tert-butyl 2-(N-(4-cyanobenzyl)-4-nitrobenzamido)acetate INT-56 as a white powder. LCMS-ESI (m/z) calculated for C21H21N3O5: 395; found 394 [M−H]−, tR=2.33 min broad (Method 10).

Workup

  1. customPrepared
  2. washwashed with NaHCO3 (2×200 mL)
  3. customThe organics were dried
  4. dry with materialover dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by chromatography (MeOH/DCM)
  7. customfollowed by evaporation from hexanes

Sources & evidence

ORD record
ord-80d417acf8ea4302825d79bc3c2c7790
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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