Benzoyl chloride → 2-(Benzhydrylidene-amino)-2-benzoyl-hex-5-enoic acid tert-butyl ester

HRID 579525Notes

Reaction equation

HRID 579525 reaction equation
[C:1]([O:5][C:6](=[O:26])[CH:7]([N:12]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][CH2:9][CH:10]=[CH2:11])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[C:37](Cl)(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1COCC1>[C:1]([O:5][C:6](=[O:26])[C:7]([N:12]=[C:13]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:37](=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:8][CH2:9][CH:10]=[CH2:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 160669741,1-Dimethylethyl 2-[(diphenylmethylene)amino]-5-hexenoate

Product 1

HCID 866637242-(Benzhydrylidene-amino)-2-benzoyl-hex-5-enoic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(benzhydrylidene-amino)-hex-5-enoic acid tert-butyl ester (350 mg, 1 mmol) in THF (5 mL, 0.2 M) was cooled to −78° C. and treated with sodium bis(trimethylsilyl)amide (2.2 mL, 1.0 M, 2.2 equiv) drop wise over 5 min and stirred for 30 min. After adding benzoyl chloride (140 μl, 1.2 mmol, 1.2 eq), the reaction mixture was warmed up to room temperature and stirred for an additional 1.5 h. The solution was cooled to 0° C. and quenched with water (5 mL). The resulting solution was diluted with ethyl acetate and washed successively with water and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. Purification by MPLC (1-40% ethyl acetate in heptane gave 2-(benzhydrylidene-amino)-2-benzoyl-hex-5-enoic acid tert-butyl ester (477 mg, 1 mmol, 100%).

Workup

  1. stirringstirred for an additional 1.5 h
  2. temperatureThe solution was cooled to 0° C.
  3. customquenched with water (5 mL)
  4. additionThe resulting solution was diluted with ethyl acetate
  5. washwashed successively with water and saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by MPLC (1-40% ethyl acetate in heptane

Sources & evidence

ORD record
ord-b217d9585daf41bb84cf645283863799
Source dataset
uspto-grants-2015_05
Patent number
US09040703B2

Reaction notes

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