Trityl chloride → HCID 18425152, compound

HRID 1280545Notes

Reaction equation

HRID 1280545 reaction equation
[NH2:1][CH:2]1[CH:5]([O:6][CH2:7][CH:8]([CH3:10])[CH3:9])[N:4]([Si](C(C)(C)C)(C)C)[C:3]1=[O:18].C(N(C(C)C)CC)(C)C.[C:28](Cl)([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C)C=O.O>[CH2:7]([O:6][CH:5]1[NH:4][C:3](=[O:18])[CH:2]1[NH:1][C:28]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[CH:8]([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 18425158HCID 18425158, compound

Product 1

HCID 18425152HCID 18425152, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (3RS,4RS)-3-amino-1-(tert-butyldimethylsilyl)-4-(isobutoxy)azetidin-2-one (0.2 g) was dissolved in dimethylformamide (8 mL), cooled in an ice bath, and treated with diisopropylethylamine (0.1 mL) followed by trityl chloride (167 mg, 0.6 mmol). The mixture was stirred for 18 h, diluted with water (40 mL) and extracted with ethyl acetate. The combined organic phase was dried (magnesium sulfate), concentrated, and the residue was chromatographed on silica gel eluted with 20% ethyl acetate:hexane to give the title compound. MS(ES) m/e 515 [M+H]+.

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic phase was dried (magnesium sulfate)
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel
  6. washeluted with 20% ethyl acetate

Sources & evidence

ORD record
ord-a73618ec1a68439890d1d61ecf6bafa0
Source dataset
uspto-grants-2002_09
Patent number
US06451785B1

Reaction notes

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