Ethyl Acetate → HCID 22988429, compound

HRID 987150Notes

Reaction equation

HRID 987150 reaction equation
[CH2:1]([N:8]([CH2:39][CH3:40])[C:9](=O)[CH:10]([O:35][CH2:36][CH3:37])[CH2:11][C:12]1[CH:34]=[CH:33][C:15]([O:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:26](=O)OC(C)(C)C)=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CSC.B.C(OC(=O)C)C.CCCCCCC>C1COCC1>[CH2:1]([N:8]([CH2:39][CH3:40])[CH2:9][CH:10]([O:35][CH2:36][CH3:37])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([NH:25][CH3:26])=[CH:23][CH:24]=2)=[CH:33][CH:34]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 12423031(Dimethyl sulfide)trihydroboronHCID 22988416HCID 22988416, compound

Product 1

HCID 22988429HCID 22988429, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 4-[2-(4-{3-[benzyl(ethyl)amino]-2-ethoxy-3-oxopropyl}phenoxy)ethyl]phenylcarbamate (5.2 g, 9.5 mmole) was dissolved in dry THF and cooled to 0° C. Borane methylsulfide (2 M, 11.9 ml, 23.8 mmole) was added dropwise. The reaction mixture was stirred at 0° C. for 0.5 hours after which it was allowed to reach room temperature and then refluxed for 5 hours. The reaction was quenched with water, extracted three times with ethyl acetate dried with magnesium sulfate and evaporated. The residue was redissolved in ethylacetate and chromatography on silica using a gradient system of ethylacetate:heptane (0-100%) gave 2.55 g (49% yield) of the desired product.

Workup

  1. customto reach room temperature
  2. temperaturerefluxed for 5 hours
  3. customThe reaction was quenched with water
  4. extractionextracted three times with ethyl acetate
  5. dry with materialdried with magnesium sulfate
  6. customevaporated
  7. dissolutionThe residue was redissolved in ethylacetate

Sources & evidence

ORD record
ord-4b5be36140a24f7dac30bb901b8802a1
Source dataset
uspto-grants-2003_10
Patent number
US06630509B2

Reaction notes

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