Sodium Carbonate → HCID 23402024, compound

HRID 1063921Notes

Reaction equation

HRID 1063921 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:34])[CH2:10][C@@:11]1([C:28]2[S:29][C:30](Br)=[CH:31][CH:32]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][N:14]([C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]1.[C:35](=[O:38])([O-])[O-].[Na+].[Na+]>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:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9](=[O:34])[CH2:10][C@@:11]1([C:28]2[S:29][C:30]([C:21]3[CH:26]=[CH:25][C:24]([C:35]4[O:38][CH:15]=[N:14][CH:13]=4)=[CH:23][CH:22]=3)=[CH:31][CH:32]=2)[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][N:14]([C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 86588737HCID 86588737, compound

Product 1

HCID 23402024HCID 23402024, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(5-oxazolyl)phenylboronic acid pinacol cyclic ester obtained in Preparation 9-2) were added N-(2-tetrahydropyranyloxy)-2-[(S)-4-benzoyl-7-(5-bromo-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (1.70 g), tetrakis(triphenylphosphine)palladium(0) (103 mg) and 2M aqueous sodium carbonate solution (5 ml) and the mixture was stirred at 80° C. for 4 hours. After evaporation of solvent, ethyl acetate and water were added and the insolubles were filtered off. The organic layer was separated, washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of chloroform and methanol (100:1 to 200:3) to give N-(2-tetrahydropyranyloxy)-2-[(S)-4-benzoyl-7-(5-(4-(5-oxazolyl)phenyl)-2-thienyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide as a pale yellow amorphous powder (1.28 g).

Workup

  1. customAfter evaporation of solvent, ethyl acetate and water
  2. additionwere added
  3. filtrationthe insolubles were filtered off
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with a mixture of chloroform and methanol (100:1 to 200:3)

Sources & evidence

ORD record
ord-d4fc774b109f4db186cd93d0773c81f3
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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