Carbamic acid, N-[(1R,2S)-1-[[(cyclopropylsulfonyl)amino]carbonyl]-2-ethenylcyclopropyl]-, 1,1-dimethylethyl ester → HCID 70324238, compound

HRID 1924365Notes

Reaction equation

HRID 1924365 reaction equation
[CH:1]1([S:4]([NH:7][C:8]([C@@:10]2([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:12][C@H:11]2[CH:13]=[CH2:14])=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1>[Ru]>[CH:1]1([S:4]([NH:7][C:8]([C@@:10]2([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:12][C@H:11]2[CH2:13][CH3:14])=[O:9])(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 45480526Carbamic acid, N-[(1R,2S)-1-[[(cyclopropylsulfonyl)amino]carbonyl]-2-ethenylcyclopropyl]-, 1,1-dimethylethyl ester

Product 1

HCID 70324238HCID 70324238, compound

Reagents, catalysts & solvents 1

HCID 23950RutheniumCatalyst

Procedure

A hydrogenation vessel was charged with a solution of tert-butyl ((1R,2S)-1-{[(cyclopropylsulfonyl)amino]carbonyl}-2-vinylcyclopropyl)carbamate (prepared as described in WO 03/099274) followed by Ru/C (7.5 wt %). The vessel was placed under N2 (20 psig) and vented to atmospheric pressure three times to remove residual oxygen. The vessel was then placed under H2 (50 psig) and the reaction was complete in <5 h based on H2 consumption. After 20 h, the vessel was vented to atmospheric pressure. The reaction slurry was then transferred out of the reaction vessel, filtered and evaporated to a yellow oil which was brought to the following step without further purification. MS (ES+) C14H24BN2O5S requires 332. Found: 333 (M+H+).

Workup

  1. customto remove residual oxygen
  2. waitthe reaction was complete in <5 h
  3. custombased on H2 consumption
  4. filtrationfiltered
  5. customevaporated to a yellow oil which
  6. customwas brought to the following step without further purification

Sources & evidence

ORD record
ord-1701bd5ec92e48abb79eaf2e00f0a2f0
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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