Diphenylacetic Acid → HCID 178522400, compound

HRID 574673Notes

Reaction equation

HRID 574673 reaction equation
[NH2:1][C:2]1[C:3]([OH:17])=[N:4][C:5]([CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:6][CH:7]=1.[C:18]1([CH:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:25](O)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH4+].[Cl-]>CN(C=O)C>[CH2:10]([O:9][CH2:8][C:5]1[N:4]=[C:3]([OH:17])[C:2]([NH:1][C:25](=[O:26])[CH:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:7][N:6]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 5

HCID 8333Diphenylacetic AcidHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178508026HCID 178508026, compound

Product 1

HCID 178522400HCID 178522400, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 3-e (1.6 g, 6.9 mmol), 2,2-diphenylacetic acid (1.47 g, 6.9 mmol), DIEA (1.8 g, 13.8 mmol), and TBTU (2.7 g, 8.28 mmol) in DMF (20 mL) was stirred at room temperature overnight. The reaction mixture was added with sat. NH4Cl (50 mL), extracted with DCM (100 mL), washed with water (50 mL) and brine ((50 mL). The organic layer was concentrated and purified by column chromatography to afford the product as a white solid, 3-f (2.2 g, 76%). 1H NMR (300 MHz, CDCl3) δ 4.45 (s, 2H), 4.63 (s, 2H), 5.07 (s, 1H), 7.27-7.40 (m, 16H), LC-MS (M+H)+ 426.1

Workup

  1. extractionextracted with DCM (100 mL)
  2. washwashed with water (50 mL) and brine ((50 mL)
  3. concentrationThe organic layer was concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-11dab23ea6ac45029f2494e28ed75576
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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