4-Bromobenzoyl chloride → 4-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)methyl)phenyl 4-bromobenzoate

HRID 923549Notes

Reaction equation

HRID 923549 reaction equation
[OH:1][C:2]1[CH:41]=[CH:40][C:5]([CH2:6][N:7]([CH2:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:8](=[O:31])[C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:30])[CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=3[C:26]([F:29])([F:28])[F:27])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[Br:42][C:43]1[CH:51]=[CH:50][C:46]([C:47](Cl)=[O:48])=[CH:45][CH:44]=1>C(Cl)Cl>[Br:42][C:43]1[CH:51]=[CH:50][C:46]([C:47]([O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:32][C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[C:8](=[O:31])[C:9]3[CH:10]=[CH:11][C:12]([NH:15][C:16](=[O:30])[CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=4[C:26]([F:28])([F:29])[F:27])=[CH:13][CH:14]=3)=[CH:40][CH:41]=2)=[O:48])=[CH:45][CH:44]=1

Participants

4

Reactant 2

HCID 685154-Bromobenzoyl chlorideHCID 71076732tert-butyl 2-(N-(4-hydroxybenzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetate

Product 1

HCID 892849964-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)methyl)phenyl 4-bromobenzoateYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Prepared using General Procedure 2: To a stirring solution of tert-butyl 2-(N-(4-hydroxybenzyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)acetate INT-9 (500 mg, 0.87 mmol) in DCM (10 mL) was added TEA (304 μL, 2.18 mmol) followed by 4-bromobenzoyl chloride (201 mg, 0.92 mmol). After 1 h, the reaction mixture was diluted with DCM (50 mL) and washed with NaHCO3 (50 mL). The organics were pre-absorbed onto silica gel and purified by chromatography (EA/isohexanes) to afford 440 mg (63%) of 4-((N-(2-(tert-butoxy)-2-oxoethyl)-4-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)benzamido)methyl)phenyl 4-bromobenzoate INT-10 as a white powder. LCMS-ESI (m/z) calculated for C37H34BrF3N2O7: 755; found 754 [M−H]−, tR=2.99 min (Method 10).

Workup

  1. customPrepared
  2. washwashed with NaHCO3 (50 mL)
  3. customThe organics were pre-absorbed onto silica gel
  4. custompurified by chromatography (EA/isohexanes)

Sources & evidence

ORD record
ord-06dbc881b8144a87bca817d7d59f5b18
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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