Acetic Acid → HCID 68685658, compound

HRID 638960Notes

Reaction equation

HRID 638960 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][N:8]([CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:9][CH:10](Cl)[CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].CC(O)=O>C1COCC1>[C:1]([O:5][C:6]([C@H:7]1[C@H:10]([CH2:11][CH3:12])[CH2:9][N:8]1[CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:27])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68684503HCID 68684503, compound

Product 1

HCID 68685658HCID 68685658, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of [benzhydryl-(2-chlorobutyl)amino]acetic acid tert-butyl ester (7.7 g, 19.9 mmol, 1 eq.) in dry THF (120 mL) at −78° C. was added NaHMDS (49.7 mL, 49.6 mmol, 2.5 eq.) dropwise over 45 min. The reaction was then neutralized with AcOH (0.2 mL). The solid formed was filtered off and washed with EtOAc and the filtrate was concentrated in vacuo. The residue was redissolved in EtOAc, washed with brine, dried over MgSO4, filtered, concentrated in vacuo. The resulting product was chromatographed on silica gel using 50% DCM/hexanes/0.5% EtOAc mixture as eluent to afford (+)-trans-1-benzhydryl-3-ethylazetidine-2-carboxylic acid tert-butyl ester 86% yield. ESMS: m/z 352.3 [M+H].

Workup

  1. customThe solid formed
  2. filtrationwas filtered off
  3. washwashed with EtOAc
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was redissolved in EtOAc
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting product was chromatographed on silica gel using 50% DCM/hexanes/0.5% EtOAc mixture as eluent

Sources & evidence

ORD record
ord-169bfe1b0e40406c80347a0c8e76519a
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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