Ethanol → HCID 70223508, compound

HRID 1531328Notes

Reaction equation

HRID 1531328 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([C@@H:18]([C:27]#[C:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@:19]([NH2:26])([O:24][CH3:25])[C:20]([O:22]C)=[O:21])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.COC1C=CC(B(O)O)=CC=1.CCO.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][C:12]([S:15]([C@@H:18]([C:27]#[C:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C@:19]([NH2:26])([O:24][CH3:25])[C:20]([OH:22])=[O:21])(=[O:17])=[O:16])=[CH:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 86756493HCID 86756493, compound

Product 1

HCID 70223508HCID 70223508, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

Methyl (2R)-{[4′-Methoxy-(1,1′-biphenyl)-4-yl]-sulfonyl}-amino-(3S)-methoxy-5-phenylpent-4ynoate: The starting sulfonamide 63f (510 mg, 1.02 mmol) and 4-methoxyphenylboronic acid (230 mg, 1.53 mmol) are taken up in 10 mL of benzene, 1.5 mL of EtOH and 1.5 mL of water in the presence of Pd(PPh3)4 (35 mg, 0.03 mmol) and 200 mg of Na2CO3 and brought to reflux for 18 hr. The mixture is cooled to room temperature, poured into water, and extracted with methylene chloride. The organic layer is dried over MgSO4, filtered and evaporated. The crude product is purified by silica gel chromatography using 9:1 hexane:EtOAc to give the desired product as a colorless oil.

Workup

  1. temperatureto reflux for 18 hr
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-bd46c0b1a61946328b62b7f10624a8f1
Source dataset
uspto-grants-2001_03
Patent number
US06197770B1

Reaction notes

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