Methyl N-(triethylammoniosulfonyl)carbamate → Ethyl (+/-)-4-(4-methoxycarbonyl-1,3-oxazolin-2-yl)-3-phenylbutanoate

HRID 989896Notes

Reaction equation

HRID 989896 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([CH2:22][OH:23])[NH:5][C:6](=O)[CH2:7][CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH3:1][O:2][C:3]([CH:4]1[CH2:22][O:23][C:6]([CH2:7][CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:5]1)=[O:24]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 53912906(+/-)-n-(4-Ethoxycarbonyl-3-phenylbutanoyl) serine methyl ester

Product 1

HCID 23389068Ethyl (+/-)-4-(4-methoxycarbonyl-1,3-oxazolin-2-yl)-3-phenylbutanoateYield 61.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (±)-N-(4-ethoxycarbonyl-3-phenylbutanoyl) serine methyl ester (723 mg, 2.14 mmole) and Burgess reagent (613 mg, 2.57 mmole) in dry THF (10 mL) was heated at reflux under N2. After 2 hr, the mixture was cooled to RT and concentrated under reduced pressure. The residue was chromatographed on silica gel (50% EtOAc/hexanes) to give the title compound (420 mg, 61%) as a colorless oil: MS (ES) m/e 320 (M+H)+.

Workup

  1. temperatureat reflux under N2
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was chromatographed on silica gel (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b69232d4a26f49fba560eec595722c19
Source dataset
uspto-grants-2002_10
Patent number
US06458814B1

Reaction notes

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