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

HRID 1879252Notes

Reaction equation

HRID 1879252 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>CO.[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

4

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 2

HCID 23950RutheniumCatalystHCID 887MethanolSolvent

Procedure

A hydrogenation vessel was charged with a solution of tert-butyl ((1R,2S)-1-{[(cyclopropylsulfonyl)amino]carbonyl}-2-vinylcyclopropyl)carbamate 87 (prepared as described in WO 03/099274) in MeOH 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 filtered and evaporated to a yellow oil which was brought to the following step without further purification. MS (ES+) m/z 333 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-a49c2842bb6b4ddd999176a9c33dad49
Source dataset
uspto-grants-2012_11
Patent number
US08314062B2

Reaction notes

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