Benzoyl chloride → HCID 58054120, compound

HRID 75124Notes

Reaction equation

HRID 75124 reaction equation
[N:1]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:7][CH2:6][CH:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[NH:4][CH2:3][CH2:2]1.[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:22]([N:4]1[CH:5]([C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9])[CH2:6][CH2:7][N:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:2][CH2:3]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 66660434Di-tert-butyl 1,4-diazepane-1,5-dicarboxylate

Product 1

HCID 58054120HCID 58054120, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Intermediate 3-2 (4.21 g) and TEA (2.0 g) in DCM (50 mL) was added benzoyl chloride (2.11 g) slowly. After stirring at room temperature for 1 hour and then the reaction was quenched with saturated sodium bicarbonate. The organic phase was dried over sodium sulfate and evaporated to dryness. Purification was achieved by chromatography on an ISCO column (RediSep 12, gradient elution with 10% to 70% EtOAc/Hex providing pure Intermediate 3-3 (2.82 g, 49% yield for the three steps).

Workup

  1. customthe reaction was quenched with saturated sodium bicarbonate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated to dryness
  4. customPurification
  5. washRediSep 12, gradient elution with 10% to 70% EtOAc/Hex

Sources & evidence

ORD record
ord-f1da4701089a4d80a71528cdbe74b5fb
Source dataset
uspto-grants-2014_09
Patent number
US08835422B2

Reaction notes

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