Sodium Carbonate → HCID 9850181, compound

HRID 2122020Notes

Reaction equation

HRID 2122020 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]([O: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.COC1C=CC(B(O)O)=CC=1.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.CCO>[CH3:37][O:36][C:33]1[CH:32]=[CH:31][C:30]([C:27]2[CH:26]=[CH:25][C:24]([S:21]([NH:20][C@H:4]([C@H:5]([O:11][CH2:12][C:13]3[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=3)[C:6]3[S:7][CH:8]=[CH:9][N:10]=3)[C:3]([OH:38])=[O:2])(=[O:23])=[O:22])=[CH:29][CH:28]=2)=[CH:35][CH:34]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 69881524HCID 69881524, compoundHCID 69882484HCID 69882484, compound

Product 1

HCID 9850181HCID 9850181, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

(2R,3S)-2-(4′-Methoxy-biphenyl-4-sulfonylamino)-3-(4-methyl-benzyloxy)-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 (590 mg, 1.12 mmol) and 4-methoxyphenylboronic acid (260 mg, 1.68 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 (40 mg, 0.03 mmol) and 237 mg of Na2CO3 and brought to reflux for 18 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 6/4 hexane/EtOAc to give the desired product as a colorless oil.

Workup

  1. temperatureto reflux for 18 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-fb77c0f4453e49ea92e1a8865471aef6
Source dataset
uspto-grants-2004_02
Patent number
US06696456B1

Reaction notes

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