Methyl N-(triethylammoniosulfonyl)carbamate → (S)-t-Butyl 2-(5-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3,4-oxadiazol-2-yl)pyrrolidine-1-carboxylate

HRID 710043Notes

Reaction equation

HRID 710043 reaction equation
[Si:1]([O:18][CH2:19][C:20]([NH:22][NH:23][C:24]([C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=O)=[O:21])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1(C)C=CC=CC=1>[Si:1]([O:18][CH2:19][C:20]1[O:21][C:24]([C@@H:26]2[CH2:30][CH2:29][CH2:28][N:27]2[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[N:23][N:22]=1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 86706754(S)-t-Butyl 2-(2-(2-((tert-butyldiphenylsilyl)oxy)acetyl)hydrazinecarbonyl)pyrrolidine-1-carboxylate

Product 1

HCID 86706755(S)-t-Butyl 2-(5-(((tert-butyldiphenylsilyl)oxy)methyl)-1,3,4-oxadiazol-2-yl)pyrrolidine-1-carboxylateYield 73.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a toluene (112 mL) solution of the compound (5.87 g) obtained in Example 9-(1), Burgess reagent (5.322 g) was added and the mixture was heated under reflux for 2.5 hours. The reaction mixture was concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (4.151 g, colorless amorphous.)

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hours
  3. concentrationThe reaction mixture was concentrated
  4. customto give a crude product, which
  5. customwas further purified by silica gel chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-49a047edf3524832b3c418e309dca408
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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