Triphenylphosphine → HCID 59608458, compound

HRID 2067161Notes

Reaction equation

HRID 2067161 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]([NH:11][CH2:12][C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=1)=[O:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:42][C:43]1[C:48]([CH2:49]O)=[CH:47][CH:46]=[CH:45][N:44]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:49][C:48]2[C:43]([CH3:42])=[N:44][CH:45]=[CH:46][CH:47]=2)=[CH:4][C:3]=1[C:9]([NH:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1)=[O:10]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 302564(2-Methylpyridin-3-yl)methanolHCID 5363146Diisopropyl azodicarboxylateHCID 59608423HCID 59608423, compound

Product 1

HCID 59608458HCID 59608458, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-({[(2-chloro-5-hydroxyphenyl)carbonyl]amino}methyl)benzoate (100 mg, 0.31 mmol) in THF (5 ml) was treated with triphenylphosphine (1.2 eq, 98 mg, 0.37 mmol), (2-methyl-3-pyridinyl)methanol (38 mg, 0.31 mmol) and diisopropylazodicarboxylate (1.2 eq, 110 ul, 0.56 mmol) and stirred at room temperature for 4 hours. Mixture diluted with methanol and purified by SCX cartridge eluting with methanol first then 2M ammonia in methanol. Basic fractions combined and evaporated to give the title compound as an off-white solid. MS (ES+) m/z 425 [M+H]+ (C23H2135ClN2O4). 1H-NMR (400 MHz, d6-DMSO) δ 3.85 (3H, s), 4.51 (2H, d, J 6), 5.18 (2H, s), 7.10-7.96 (9H, m), 8.42 (1H, dd, J 1.6, J 4.8), 9.07 (1H, t, J 6).

Workup

  1. custompurified by SCX cartridge
  2. washeluting with methanol first
  3. customevaporated

Sources & evidence

ORD record
ord-7fd52e5235464b8ca6d95387ffeb38eb
Source dataset
uspto-grants-2012_10
Patent number
US08293798B2

Reaction notes

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