HCID 87100313, compound → HCID 86596706, compound

HRID 422926Notes

Reaction equation

HRID 422926 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:40])([CH2:20][CH2:21][C:22]1[N:23]([CH3:39])[C:24]([C:27](=[O:38])[CH2:28][CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:25][CH:26]=1)[CH:10]=[CH:11][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:40])([CH2:20][CH2:21][C:22]1[N:23]([CH3:39])[C:24]([C:27](=[O:38])[CH2:28][CH2:29][CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:25][CH:26]=1)[CH2:10][CH2:11][P:12](=[O:19])([O:13][CH2:14][CH3:15])[O:16][CH2:17][CH3:18])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 87100313HCID 87100313, compound

Product 1

HCID 86596706HCID 86596706, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)Catalyst2×HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of diethyl (3R)-3-t-butoxycarbonylamino-3-methyl-5-[1-methyl-5-(5-phenylpentanoyl)pyrrol-2-yl]pent-1-enylphosphonate (145.4 mg, 0.25 mmol) obtained in Example (44b) in ethanol (2.5 ml) was added chlorotris(triphenylphosphine)rhodium(I) (23.7 mg, 0.026 mmol), and the resulting mixture was stirred at 50° C. under a hydrogen atmosphere for 5 hours. After cooling, to the reaction mixture was added furthermore chlorotris(triphenylphosphine)rhodium(I) (24.3 mg, 0.026 mmol), and the resulting mixture was stirred at 50° C. under a hydrogen atmosphere for 5 hours. After stirring, the reaction mixture was evaporated in vacuo, and the residue was purified by chromatography on a silica gel column using ethyl acetate as the eluent to afford the crude product (154.0 mg). Furthermore, the crude product obtained was purified using a preparative reversed phase HPLC column [Inertsil ODS-3 (2.0 cm×25 cm), GL Science, mobile phase: acetonitrile/water (80:20), flow rate: 10 ml/min] to afford the title compound (116.1 mg, yield: 80%).

Workup

  1. temperatureAfter cooling, to the reaction mixture
  2. stirringthe resulting mixture was stirred at 50° C. under a hydrogen atmosphere for 5 hours
  3. stirringAfter stirring
  4. customthe reaction mixture was evaporated in vacuo
  5. customthe residue was purified by chromatography on a silica gel column
  6. customto afford the crude product (154.0 mg)
  7. customFurthermore, the crude product obtained
  8. customwas purified

Sources & evidence

ORD record
ord-aaf201ebe0b44b188ac108acf41388db
Source dataset
uspto-grants-2012_01
Patent number
US08101650B2

Reaction notes

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