HCID 60077664, compound → HCID 60077679, compound

HRID 2084455Notes

Reaction equation

HRID 2084455 reaction equation
[NH2:1]/[C:2](=[N:20]\[O:21][C:22]([C@H:24]([CH2:33][CH2:34][CH2:35][CH:36]1[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]1)[CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=O)/[CH:3]1[CH2:6][N:5]([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4]1>C1(C)C=CC=CC=1>[CH:7]([N:5]1[CH2:6][CH:3]([C:2]2[N:1]=[C:22]([C@H:24]([CH2:33][CH2:34][CH2:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:25][C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[O:21][N:20]=2)[CH2:4]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 60077664HCID 60077664, compound

Product 1

HCID 60077679HCID 60077679, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of tert-butyl (3R)-3-[({[(Z)-amino(1-benzhydryl-3-azetidinyl)methylidene]amino}oxy)carbonyl]-6-cyclohexylhexanoate (preparation 35) (2.85 g, 5.07 mmol) in toluene (90 ml) was heated at 140° C. under Dean and Stark conditions for 18 hours. The reaction mixture was allowed to cool to room temperature. The solvent was removed under reduced pressure. The residue was purified on a silica column eluting with a solvent gradient of cyclohexane:Et2O (90:10) gradually changing to (60:40) to afford the title compound as a colourless oil (2.0 g, 73%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified on a silica column
  3. washeluting with a solvent gradient of cyclohexane:Et2O (90:10)

Sources & evidence

ORD record
ord-e9956960a5f143549bf66687c3aee5b4
Source dataset
uspto-grants-2004_04
Patent number
US06716861B2

Reaction notes

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