Sodium bis(trimethylsilyl)amide → Methyl 7-(N-(4-(1-(4-methoxybenzyloxy)hexyl)phenyl)acetamido)hept-5-ynoate

HRID 1015459Notes

Reaction equation

HRID 1015459 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][O:12][C:13]1[CH:36]=[CH:35][C:16]([CH2:17][O:18][CH:19]([C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:34])[CH3:33])=[CH:27][CH:26]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:15][CH:14]=1.I[CH2:38][C:39]#[C:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45]>C1COCC1>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][O:18][CH:19]([C:25]2[CH:26]=[CH:27][C:28]([N:31]([CH2:38][C:39]#[C:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45])[C:32](=[O:34])[CH3:33])=[CH:29][CH:30]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 10901527Methyl 7-iodohept-5-ynoateHCID 59728274N-(4-(1-(4-methoxybenzyloxy)hexyl)phenyl)acetamide

Product 1

HCID 59728267Methyl 7-(N-(4-(1-(4-methoxybenzyloxy)hexyl)phenyl)acetamido)hept-5-ynoateYield 25.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Sodium bis(trimethylsilyl)amide (0.31 ml of a 1.0 M solution in THF, 0.31 mmol) was added to a solution of the aryl amide 103 (100 mg, 0.282 mmol) in THF (1.3 mL) at 0° C. After 15 min a solution of the methyl 7-iodohept-5-ynoate (90 mg, 0.338 mmol) in THF (0.3 mL) was added and the reaction was warmed room temperature. After stirring for 16 h the reaction was the quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The organic portion was washed with brine, dried (MgSO4), filtered and the filtrate was concentrated in vacuo. Purification by FCC (silica gel, 3:2 hex/EtOAc) gave 35 mg (25%) of ester 104.

Workup

  1. customquenched with saturated aqueous ammonium chloride
  2. extractionextracted with EtOAc
  3. washThe organic portion was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customPurification by FCC (silica gel, 3:2 hex/EtOAc)

Sources & evidence

ORD record
ord-ea88072c23bc40818eb850de148115f5
Source dataset
uspto-grants-2011_07
Patent number
US07985767B2

Reaction notes

Loading…