tert-Butanol → HCID 69212984, compound

HRID 2375760Notes

Reaction equation

HRID 2375760 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([OH:24])=[O:23])=[CH:17][CH:16]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(OCC)=O.C(N(CC)CC)C.[C:38](O)([CH3:41])([CH3:40])[CH3:39]>C(Cl)(Cl)Cl>[CH3:39][C:38]([O:23][C:22](=[O:24])[CH2:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:10])=[CH:20][CH:19]=1)([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 22994173HCID 22994173, compound

Product 1

HCID 69212984HCID 69212984, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of 3 g (9.1 mmol) of 4-[2-[[(phenylmethoxy)carbonyl]amino]-ethoxy]benzeneacetic acid in 60 ml of chloroform is cooled to −30° C. and 1.18 g (10.9 mmol) of ethyl chloroformate and 1.52 ml (10.9 mmol) of triethylamine are added. The mixture is stirred for 1 hour at −30° C. and 1.63 g (22 mmol) of t-butanol and 1.52 ml (10.9 mmol) of triethylamine are then added. The mixture is stirred for 16 hours at room temperature and then concentrated under reduced pressure. The evaporation residue is taken up in 100 ml of ethyl acetate and the organic phase obtained is washed with water and then dried over magnesium sulfate and concentrated under reduced pressure. The crude product is purified by chromatography on silica gel using a dichloromethane/methylcyclohexane mixture (1/1; v/v) as the eluent to give 930 mg of the expected compound (yield=26%).

Workup

  1. stirringThe mixture is stirred for 16 hours at room temperature
  2. concentrationconcentrated under reduced pressure
  3. customthe organic phase obtained
  4. washis washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by chromatography on silica gel using a dichloromethane/methylcyclohexane mixture (1/1; v/v) as the eluent

Sources & evidence

ORD record
ord-6df0c8e71a414521a45cc43be3f3165b
Source dataset
uspto-grants-2008_12
Patent number
US07465811B2

Reaction notes

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