Methyl N-(triethylammoniosulfonyl)carbamate → (S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)oxazol-2-yl)pyrrolidine-1-carboxylate

HRID 710064Notes

Reaction equation

HRID 710064 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[O:6][CH2:7][C:8](=[O:25])[CH2:9][NH:10][C:11]([C@@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=O.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[O:6][CH2:7][C:8]1[O:25][C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 86706777(S)-tert-Butyl 2-((3-(3,4-dimethoxyphenoxy)-2-oxopropyl)carbamoyl)pyrrolidine-1-carboxylate

Product 1

HCID 86706778(S)-t-Butyl 2-(5-((3,4-dimethoxyphenoxy)methyl)oxazol-2-yl)pyrrolidine-1-carboxylateYield 65.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a toluene (10 ml) of the compound (0.250 g) obtained in Example 19-(4), Burgess reagent (0.281 g) was added and the mixture was stirred at 50° C. for 1.5 hours. After reversion to room temperature, 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 (0.156 g, colorless oil.)

Workup

  1. concentrationAfter reversion to room temperature, the reaction mixture was concentrated
  2. customto give a crude product, which
  3. customwas further purified by silica gel chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-2feb28c0581541feb95afde1a4745eaf
Source dataset
uspto-grants-2015_11
Patent number
US09181229B2

Reaction notes

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