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Methyl N-(triethylammoniosulfonyl)carbamate → 2-[4-(N-tert-butoxycarbonylamino-methyl)-phenyl]-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

HRID 2221438
Notes
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Reaction equation

HRID 2221438 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[CH:25]=[CH:24][C:13]([C:14]([NH:16][CH:17]([CH2:22]O)[C:18]([O:20][CH3:21])=[O:19])=[O:15])=[CH:12][CH:11]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[C:1]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]2[O:15][CH2:22][CH:17]([C:18]([O:20][CH3:21])=[O:19])[N:16]=2)=[CH:24][CH:25]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 69202136HCID 69202136, compound

Product 1

HCID 692000722-[4-(N-tert-butoxycarbonylamino-methyl)-phenyl]-4,5-dihydro-oxazole-4-carboxylic acid methyl esterYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 2-[4-(N-Boc-aminomethyl)benzoylamino]-3-hydroxypropionate (32.0 g, 90.8 mmol) in THF (150 ml) was added Burgess' Reagent (26.0 g, 109 mmol) and 3 Å molecular sieves (1 g). The reaction was allowed to stir at 60° C. for 2 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The crude product was dissolved in dichloromethane and purified by flash chromatography over silica gel with ethyl acetate/dichloromethane (1/1) to give methyl 2-[4-(N-Boc-aminomethyl)-phenyl]-4,5-dihydrooxazol-4-ylcarboxylate (29.5 g, 88.2 mmol) as a pale tan oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude product was dissolved in dichloromethane
  4. custompurified by flash chromatography over silica gel with ethyl acetate/dichloromethane (1/1)

Sources & evidence

ORD record
ord-61f5c48fac01495a985ffb234dd91d0d
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07368572B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes