4-tert-Butylbenzoic acid → HCID 117740971, compound

HRID 1775871Notes

Reaction equation

HRID 1775871 reaction equation
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1)[C:3]([O:5][CH3:6])=[O:4].[C:14]([C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:13][C:10]1[CH:9]=[CH:8][C:7]([CH:2]([NH:1][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:18]([C:14]([CH3:16])([CH3:15])[CH3:17])=[CH:19][CH:20]=2)[C:3]([O:5][CH3:6])=[O:4])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 74034-tert-Butylbenzoic acidHCID 81531DiisopropylethylamineHCID 2764323Methyl α-amino-4-bromobenzeneacetateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 117740971HCID 117740971, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Prepared using General Procedure 7. To a stirring solution of methyl 2-amino-2-(4-bromophenyl)acetate (421 mg, 1.5 mmol), 4-(tert-butyl)benzoic acid (321 mg, 1.8 mmol), and DIEA (831 μl, 4.5 mmol) in DMF (3 mL) cooled to 0° C. was slowly added a solution of HATU (380 mg, 1.65 mmol) in DMF (1.5 mL) in a drop-wise fashion. The reaction mixture was allowed to warm slowly and stirring continued for 4 h. The reaction mixture was poured onto ice-water and the solid was filtered. The solid was dissolved in DCM (10 mL), dried over MgSO4 and evaporated to afford 532 mg (88%) of methyl 2-(4-bromophenyl)-2-(4-(tert-butyl)benzamido)acetate. LCMS-ESI (m/z) calculated for C20H22BrNO3: 403.0. found 404.1 [M+H]+, tR=3.61 min. (Method 16).

Workup

  1. customPrepared
  2. temperatureto warm slowly
  3. additionThe reaction mixture was poured onto ice-water
  4. filtrationthe solid was filtered
  5. dissolutionThe solid was dissolved in DCM (10 mL)
  6. dry with materialdried over MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-9159f39f08a74649ad1c0e1e8356b24e
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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