3-Hydroxybenzaldehyde → HCID 178420765, compound

HRID 1993116Notes

Reaction equation

HRID 1993116 reaction equation
[O-:1]S(C(F)(F)F)(=O)=O.OC1C=[C:12](C=CC=1)[CH:13]=[O:14].C1CN([P+:23]([O:34]N2N=[N:42][C:37]3C=[CH:39][CH:40]=[CH:41][C:36]2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN([CH:57]([CH3:59])C)C(C)C>CN(C=O)C>[NH:42]1[CH:39]=[CH:40][CH2:41][CH2:36][CH2:37]1.[PH:23](=[O:34])([O:14][CH2:13][CH3:12])[O:1][CH2:57][CH3:59]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 2758875Trifluoromethanesulfonate

Product 1

HCID 178420765HCID 178420765, compoundYield 278.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of compound 10 (1 g, 1.3 mmol) in 6 mL of DMF at room temperature under N2 was added 3-hydroxybenzaldehyde (292 mg, 2.6 mmol) and PyBOP (1 g, 1.95 mmol), followed by DIEA (0.9 mL, 5.2 mmol). After 5 h, the solvent was removed under reduced pressure, and the resulting crude mixture was purified by chromatography on silica gel (ethyl acetate/hexane 1:1) to give 11 (800 mg, 70%) as a white solid. 1H NMR (CDCl3) δ 9.98 (s, 1H), 7.79-6.88 (m, 12H), 5.65 (m, 1H), 5.21-4.99 (m, 3H), 4.62-4.16 (m, 4H), 3.99-3.61 (m overlapping s, 9H), 3.11-2.79 (m, 5H), 1.85-1.53 (m, 6H), 1.25 (m, 3H), 0.90 (m, 6H); 31P NMR (CDCl3) δ 17.9 and 15.9; MS (ESI) 899 (M+Na).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe resulting crude mixture was purified by chromatography on silica gel (ethyl acetate/hexane 1:1)

Sources & evidence

ORD record
ord-2eee6c29181f4d07b823a52baa2fc6df
Source dataset
uspto-grants-2010_01
Patent number
US07649015B2

Reaction notes

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