Diisopropylethylamine → HCID 67018182, compound

HRID 1671675Notes

Reaction equation

HRID 1671675 reaction equation
[C:1]([NH:8][CH2:9][CH:10]1[CH2:13][CH2:12][NH:11]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(C(C)C)C(C)C.[C:23]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:24]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=1>CN(C=O)C.CC(=O)OCC>[C:4]([O:3][C:1](=[O:2])[NH:8][CH2:9][CH:10]1[CH2:13][CH2:12][N:11]1[S:29]([C:24]1[C:23]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:31])=[O:30])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27566802-Phenylbenzene-1-sulfonyl chlorideHCID 14280902tert-Butyl [(azetidin-2-yl)methyl]carbamate

Product 1

HCID 67018182HCID 67018182, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cold (5° C.) solution of 2-(N-Boc-aminomethyl) azetidine (200 mg), DIEA (0.375 mL) in dry DMF (2 mL), was added portionwise biphenyl-2-sulfonyl chloride (272 mg). The reaction mixture was stirred at RT for 20 h. The reaction mixture was diluted with EA, washed with water. The organic extract was dried (MgSO4), filtered and concentrated to yield the crude product as light brown oil (295 mg, 68%) which was used for the next step without further purification.

Workup

  1. washwashed with water
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-61180db9338646299f9e7d1575a566b2
Source dataset
uspto-grants-2011_08
Patent number
US07994336B2

Reaction notes

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