Ethanol → HCID 9872387, compound

HRID 2122022Notes

Reaction equation

HRID 2122022 reaction equation
C[O:2][C:3](=[O:38])[C@H:4]([NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([S:36][CH3:37])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)(=[O:23])=[O:22])[C@H:5]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)[C:6]1[S:7][CH:8]=[CH:9][N:10]=1.COC(=O)[C@H](NS(C1C=CC(Br)=CC=1)(=O)=O)[C@H](OCC1C=CC(C)=CC=1)C1SC=CN=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>[CH3:19][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][O:11][C@H:5]([C:6]2[S:7][CH:8]=[CH:9][N:10]=2)[C@@H:4]([NH:20][S:21]([C:24]2[CH:25]=[CH:26][C:27]([C:30]3[CH:35]=[CH:34][C:33]([S:36][CH3:37])=[CH:32][CH:31]=3)=[CH:28][CH:29]=2)(=[O:22])=[O:23])[C:3]([OH:38])=[O:2])=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 69881128HCID 69881128, compoundHCID 69881524HCID 69881524, compound

Product 1

HCID 9872387HCID 9872387, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

(2R,3S)-3-(4-Methyl-benzyloxy)-2-(4′-methylsulfanyl-biphenyl-4-sulfonylamino)-3-thiazol-2-yl-propionic acid methyl ester. The (2R,3S)-2-(4-bromo-benzenesulfonylamino)-3-(4-methyl-benzyloxy)-3-thiazol-2-yl-propionic acid methyl ester 1e (660 mg, 1.26 mmol) and 4-thiomethoxyphenylboronic acid (320 mg, 1.88 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 (44 mg, 0.03 mmol) and 267 mg of Na2CO3 and brought to reflux for 4 hours. The mixture is cooled to room temperature, poured into water, and extracted with methylene chloride. The organic layer is dried over Na2SO4, filtered and evaporated. The crude product is purified by silica gel chromatography using 8/2 hexane/EtOAc to give the desired product as a colorless oil.

Workup

  1. temperatureto reflux for 4 hours
  2. extractionextracted with methylene chloride
  3. dry with materialThe organic layer is dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-fb2478938c42492b84451f45ebcdb57a
Source dataset
uspto-grants-2004_02
Patent number
US06696456B1

Reaction notes

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