Benzoic Acid → HCID 70496724, compound

HRID 1045490Notes

Reaction equation

HRID 1045490 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.CCN(C(C)C)C(C)C.[NH2:34][C:35]1[CH:57]=[CH:56][C:38]([CH2:39][NH:40][C:41]2[C:46]3[CH:47]4[O:55][CH2:54][CH2:53][CH2:52][N:48]4[C:49](=[O:51])[NH:50][C:45]=3[N:44]=[CH:43][CH:42]=2)=[CH:37][C:36]=1[F:58]>CN(C=O)C>[F:58][C:36]1[CH:37]=[C:38]([CH2:39][NH:40][C:41]2[C:46]3[CH:47]4[O:55][CH2:54][CH2:53][CH2:52][N:48]4[C:49](=[O:51])[NH:50][C:45]=3[N:44]=[CH:43][CH:42]=2)[CH:56]=[CH:57][C:35]=1[NH:34][C:1](=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 70498233HCID 70498233, compound

Product 1

HCID 70496724HCID 70496724, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzoic acid (35 mg; 0.17 mmol), Bop-Cl (39 mg; 0.16 mmol), DIEA (0.04 mL; 0.25 mmol), and 45 (55mg, 0.26 mmol) were suspended in DMF (2 mL), and stirred overnight at room temperature. The crude reaction mixture was purified directly via HPLC to provide 52 (7 mg, 10% yield) as a solid. LC-MS (M+H=448, obsd.=448).

Workup

  1. customThe crude reaction mixture
  2. customwas purified directly via HPLC

Sources & evidence

ORD record
ord-d151819271024141ad6b82b1ced3a966
Source dataset
uspto-grants-2013_10
Patent number
US08569295B2

Reaction notes

Loading…