Water → tert-butyl (6R,7R)-6-{[(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]methyl}-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

HRID 1022689Notes

Reaction equation

HRID 1022689 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][C@H:10]2[CH2:23][NH:24][CH2:25][CH2:26][OH:27])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[C:35]([Si:39](Cl)([CH3:41])[CH3:40])([CH3:38])([CH3:37])[CH3:36].O>C1COCC1>[Si:39]([O:27][CH2:26][CH2:25][NH:24][CH2:23][C@H:10]1[C@H:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[O:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:11]1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 28928tert-Butyldimethylsilyl chloride2×HCID 66975933tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-{[(2-hydroxyethyl)amino]methyl}-1,4-oxazepane-4-carboxylate

Product 1

HCID 66974980tert-butyl (6R,7R)-6-{[(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]methyl}-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylateYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution (13.2 mL) of tert-butyl (6R,7R)-7-(3,4-dichlorophenyl)-6-{[(2-hydroxyethyl)amino]methyl}-1,4-oxazepane-4-carboxylate (1.65 g) and triethylamine (0.605 mL) in THF was added, under ice-cooling, tert-butylchlorodimethylsilane (654 mg), and the mixture was stirred at room temperature overnight. Then, tert-butylchlorodimethylsilane (654 mg) and triethylamine (0.605 mL) were added, and the mixture was stirred at 50° C. for 1 hr. Distilled water was added, and the mixture was extracted with ethyl acetate. The extract was washed with distilled water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (1.96 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with distilled water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0e3eeccc88b240319b19f193c3cb2bef
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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