2,6-Dimethoxybenzoyl chloride → HCID 118308097, compound

HRID 1750489Notes

Reaction equation

HRID 1750489 reaction equation
[CH:1]1([NH:5][C@H:6]2[CH2:10][CH2:9][CH2:8][C@@H:7]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[CH3:28][O:29][C:30]1[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[C:31]=1[C:32](Cl)=[O:33]>C(Cl)Cl>[CH:1]1([N:5]([C@H:6]2[CH2:10][CH2:9][CH2:8][C@@H:7]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[C:32](=[O:33])[C:31]2[C:35]([O:39][CH3:40])=[CH:36][CH:37]=[CH:38][C:30]=2[O:29][CH3:28])[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 81531DiisopropylethylamineHCID 118308201HCID 118308201, compound

Product 1

HCID 118308097HCID 118308097, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl N-[(1S,2S)-2-(cyclobutylamino)cyclopentyl]carbamate (400 mg, 1.573 mmol) in dry DCM (5.3 ml) was added DIPEA (1.3 ml, 7.86 mmol) and 2,6-dimethoxybenzoyl chloride (CAS number 1989-53-3; 473 mg, 2.359 mmol). The reaction was stirred at room temperature for 1 hour and was then partitioned between DCM and water, filtered through a hydrophobic frit and concentrated in vacuo. This was then purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customwas then partitioned between DCM and water
  2. filtrationfiltered through a hydrophobic frit
  3. concentrationconcentrated in vacuo
  4. customThis was then purified by column chromatography (basic silica, 0-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-d6367b109b5b4719ba6c0faa19a66b05
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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