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4-Nitro-benzoic acid 5-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidin-3-yl ester → 18-Hydroxy-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo-[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl ester

HRID 1429126
Notes
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Reaction equation

HRID 1429126 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[N:18]([C:19](=[O:37])[N:20]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]=[CH2:36])[CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[CH2:17][CH:16]([O:38]C(=O)C3C=CC([N+]([O-])=O)=CC=3)[CH2:15]2)=[O:13])[CH2:8][CH:7]1C=C)=[O:5])[CH3:2]>ClCCCl>[CH2:1]([O:3][C:4]([C:6]12[CH2:8][CH:7]1[CH:36]=[CH:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][N:20]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)[C:19](=[O:37])[N:18]1[CH:14]([CH2:15][CH:16]([OH:38])[CH2:17]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 668705064-Nitro-benzoic acid 5-(1-ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-1-[hept-6-enyl-(4-methoxy-benzyl)-carbamoyl]-pyrrolidin-3-yl ester

Product 1

HCID 6687090918-Hydroxy-14-(4-methoxy-benzyl)-2,15-dioxo-3,14,16-triaza-tricyclo-[14.3.0.0*4,6*]nonadec-7-ene-4-carboxylic acid ethyl esterYield 61%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 2a (1 g, 1.48 mmol) was dissolved in 1,2-dichloroethane (2 l). The mixture was degassed for 15 min using a stream of argon. Hoveyda-Grubbs catalyst (II) (50 mg, 5 mol %) was added and the mixture was refluxed for 4 h. The solvent was evaporated and the crude ester was dissolved in THF (100 ml), methanol (50 ml) and water (50 ml). The mixture was cooled to 0° C. on an ice-bath. Aqueous lithium hydroxide (20 ml, 1M) was added and the mixture was stirred at 0° C. for 4 h. The volume was then doubled by addition of water and the mixture was acidified with acetic acid. Extraction (dichloromethane) followed by flash column chromatography (methanol 1→5% in ether) gave pure title compound (450 mg, 61%).

Workup

  1. customThe mixture was degassed for 15 min
  2. additionHoveyda-Grubbs catalyst (II) (50 mg, 5 mol %) was added
  3. temperaturethe mixture was refluxed for 4 h
  4. customThe solvent was evaporated
  5. dissolutionthe crude ester was dissolved in THF (100 ml)
  6. additionAqueous lithium hydroxide (20 ml, 1M) was added
  7. additionThe volume was then doubled by addition of water
  8. extractionExtraction (dichloromethane)

Sources & evidence

ORD record
ord-33adbe3f4fdc4dd9b13ee2b38724cd70
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937080B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes