HCID 12045576, compound → HCID 70029841, compound

HRID 1862547Notes

Reaction equation

HRID 1862547 reaction equation
B.CSC.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[N:15]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:14](=O)[C@@H:13]([CH2:22][C:23](O)=[O:24])[O:12][C@H:11]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]4[O:32][CH2:33][CH2:34][O:35][C:27]=34)[C:10]=2[CH:36]=1>O1CCCC1>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]2[N:15]([CH2:16][C:17]([CH3:19])([CH3:20])[CH3:18])[CH2:14][C@@H:13]([CH2:22][CH2:23][OH:24])[O:12][C@H:11]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]4[O:32][CH2:33][CH2:34][O:35][C:27]=34)[C:10]=2[CH:36]=1

Participants

4

Reactant 2

HCID 12045576HCID 12045576, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 70029841HCID 70029841, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulfide complex (2.0M in tetrahydrofuran; 5.9 mL, 11.8 mmol) was added to a solution of the ethyl ester of trans-7-chloro-5-(2,3-ethylenedioxyphenyl)-1-neopentyl-1,2,3,5-tetrahydro-2-oxo-4,1-benzoxazepine-3-acetic acid (1.44 g, 2.95 mmol; Example 1D) in tetrahydrofuran (4.4 mL) under a nitrogen atmosphere. The reaction was stirred at ambient temperature for 18 hours and then cooled to 0° C. and quenched by slow addition of methanol. Once gas evolution ceased, an additional amount of methanol was added and the resulting mixture stirred 1 hour. The reaction mixture was then concentrated and the resulting residue taken up in water and extracted with ethyl acetate (3×). The combined organics were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by flash column chromatography (3:1 hexanes/ethyl acetae) to give 835 mg (66%) of the title compound as a white solid.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched by slow addition of methanol
  3. additionan additional amount of methanol was added
  4. stirringthe resulting mixture stirred 1 hour
  5. concentrationThe reaction mixture was then concentrated
  6. extractionextracted with ethyl acetate (3×)
  7. washThe combined organics were washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. custompurified by flash column chromatography (3:1 hexanes/ethyl acetae)

Sources & evidence

ORD record
ord-928229c1fae84ed9a3d3cc0108b11ad0
Source dataset
uspto-grants-2003_03
Patent number
US06537987B1

Reaction notes

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