Ethanol → HCID 70224410, compound

HRID 1531329Notes

Reaction equation

HRID 1531329 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:33]#[C:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@:19]([NH2:32])([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[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:33]#[C:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C@:19]([NH2:32])([O:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]([OH:22])=[O:21])(=[O:16])=[O:17])=[CH:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 86756494HCID 86756494, compound

Product 1

HCID 70224410HCID 70224410, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

Methyl (2R)-{[4′-Methoxy-(1,1′-biphenyl)-4-yl]-sulfonyl}-amino-(3S)-benzyl-oxy-5-phenyl-pent-4-ynoate: The starting sulfonamide 65e (927 mg, 1.75 mmol) and 4-methoxyphenylboronic acid (400 mg, 2.63 mmol) are taken up in 25 mL of benzene, 1.5 mL of EtOH and 1.5 mL of water in the presence of Pd(PPh3)4 (61 mg, 0.05 mmol) and 371 mg of Na2CO3 and brought to reflux for 4 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 4 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-31b042f966114f72bbe1bf8895f22c5d
Source dataset
uspto-grants-2001_03
Patent number
US06197770B1

Reaction notes

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