Imidazole → 3-(t-Butoxycarbonylamino)-2-hydroxypropyl Triisopropylsilyl Ether

HRID 1434861Notes

Reaction equation

HRID 1434861 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([OH:13])[CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[CH:19]([Si:22](Cl)([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])([CH3:21])[CH3:20]>CN(C=O)C>[CH:19]([Si:22]([O:12][CH2:11][CH:10]([OH:13])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 4206999tert-butyl N-(2,3-dihydroxypropyl)carbamate

Product 1

HCID 579366063-(t-Butoxycarbonylamino)-2-hydroxypropyl Triisopropylsilyl EtherYield 151.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. mixture of 3-(t-butoxycarbonylamino)-2-hydroxypropanol (22.5 g, 118 mmol), imidazole (8.8 g, 130 mmol) and DMF (450 ml) was added triisopropylsilyl chloride (25 mL, 118 mmol). The reaction was warmed to room temperature and stirred for 3 h. The reaction was concentrated to a slurry, CH2Cl2 was added, and the mixture filtered. The filtrate was washed with water (2×) and concentrated. The reaction was repeated. The combined crude product was chromatographed with SiO2 (hexanes to 30% EtOAc/hexanes) to give the title compound (62.2 g, 76%).

Workup

  1. concentrationThe reaction was concentrated to a slurry, CH2Cl2
  2. additionwas added
  3. filtrationthe mixture filtered
  4. washThe filtrate was washed with water (2×)
  5. concentrationconcentrated
  6. customwas chromatographed with SiO2 (hexanes to 30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a91758b4c98c4f5baf14f30bd9c9d5d8
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

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