Triethylamine → tert-butyl (6R,7S)-7-(3,4-dichlorophenyl)-6-({[2-(trimethylsilyl)ethoxy]carbonyl}amino)-1,4-oxazepane-4-carboxylate

HRID 1022618Notes

Reaction equation

HRID 1022618 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][C@@H:13](C(O)=O)[C@H:12]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[O:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.C([N:45]([CH2:48]C)CC)C.[CH3:50][Si:51]([CH3:56])([CH3:55])[CH2:52][CH2:53][OH:54]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:25][C:20]1[CH:19]=[C:18]([C@@H:12]2[O:11][CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:14][C@H:13]2[NH:45][C:48]([O:54][CH2:53][CH2:52][Si:51]([CH3:56])([CH3:55])[CH3:50])=[O:33])[CH:23]=[CH:22][C:21]=1[Cl:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 66975341(6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid

Product 1

HCID 66975344tert-butyl (6R,7S)-7-(3,4-dichlorophenyl)-6-({[2-(trimethylsilyl)ethoxy]carbonyl}amino)-1,4-oxazepane-4-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (6R,7R)-4-(tert-butoxycarbonyl)-7-(3,4-dichlorophenyl)-1,4-oxazepane-6-carboxylic acid (1.0 g) in toluene (10 mL) were added diphenylphosphoryl azide (0.828 mL) and triethylamine (0.536 mL) at room temperature, and the mixture was stirred at 90° C. for 30 min. To the reaction mixture was added 2-(trimethylsilyl)ethanol (0.727 mL) at 90° C., and the mixture was stirred at 90° C. for 2 hr. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (0.67 g).

Workup

  1. stirringthe mixture was stirred at 90° C. for 2 hr
  2. washThe diluted solution was washed with distilled water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-76baf779f2fe42e4a048b927e074d1d5
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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