Diisopropylethylamine → (1R,3S)-3-(tert-butoxycarbonyl)-2,2-dimethylcyclobutanecarboxylic 2,4,6-trichlorobenzoic anhydride

HRID 2179732Notes

Reaction equation

HRID 2179732 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[CH2:11][C@@H:10]([C:12]([OH:14])=[O:13])[C:9]1([CH3:16])[CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[C:28]=1[C:29](Cl)=[O:30]>C1COCC1>[Cl:26][C:27]1[CH:35]=[C:34]([Cl:36])[CH:33]=[C:32]([Cl:37])[C:28]=1[C:29]([O:13][C:12]([C@@H:10]1[CH2:11][C@H:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:9]1([CH3:16])[CH3:15])=[O:14])=[O:30]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 21576611(1R,3S)-3-[(tert-Butoxy)carbonyl]-2,2-dimethylcyclobutane-1-carboxylic acid

Product 1

HCID 86650109(1R,3S)-3-(tert-butoxycarbonyl)-2,2-dimethylcyclobutanecarboxylic 2,4,6-trichlorobenzoic anhydride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (1R,3S)-3-(tert-butoxycarbonyl)-2,2-dimethylcyclobutanecarboxylic acid (about 0.450 g, 1.97 mmol) and DIPEA (about 1.01 ml, 5.92 mmol) in THF (about 4 ml) and 2,4,6-trichloro benzoyl chloride (0.35 ml, 2.17 mmol) were added at 0° C. and the reaction mixture was allowed to stir at room temperature for about 6 hours, after completion of the reaction (monitored by TLC), the solvent was evaporated and crude product proceeded as such for the next reaction.

Workup

  1. customafter completion of the reaction (monitored by TLC)
  2. customthe solvent was evaporated
  3. customsuch for the next reaction

Sources & evidence

ORD record
ord-e5b0dd68cdd448adb4d4f436e53c9182
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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