Sodium Bicarbonate → HCID 11407837, compound

HRID 602744Notes

Reaction equation

HRID 602744 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]([S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])([CH:6]1[CH2:11][CH2:10][CH2:9][C:8](=O)[CH2:7]1)[CH3:5].Cl.[Cl:24][C:25]1[N:30]=[CH:29][C:28]([NH:31]N)=[CH:27][CH:26]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:22])[C:4]([S:13]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)(=[O:14])=[O:15])([CH:6]1[CH2:7][C:8]2[NH:31][C:28]3[CH:27]=[CH:26][C:25]([Cl:24])=[N:30][C:29]=3[C:9]=2[CH2:10][CH2:11]1)[CH3:5]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 67266871(RS,SR)-2-benzenesulfonyl-2-(3-oxo-cyclohexyl)-propionic acid methyl esterHCID 86600792HCID 86600792, compound

Product 1

HCID 11407837HCID 11407837, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
115 °C

Procedure

In a sealed tube, 50 mg (0.15 mmol) of (RS,SR)-2-benzenesulfonyl-2-(3-oxo-cyclohexyl)-propionic acid methyl ester in 4 mL of glacial acetic acid were treated with 27 mg (0.18 mmol, 1.2 eq) of (6-chloro-pyridin-3-yl)-hydrazine hydrochloride and stirred at 115° C. for 3 hours. An aqueous solution of NaHCO3 was added until pH=7 was reached, and the mixture was extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. A column chromatography on silica gel with heptane/EtOAc 1:1 followed by trituration with Et2O yielded 52 mg (76%) of (RS,SR)-2-benzenesulfonyl-2-(2-chloro-6,7,8,9-tetrahydro-5H-pyrido[3,2-b]indol-7-yl)-propionic acid methyl ester as a white solid, MS: 433 (MH+).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-d0ab472c611540d29c6aabd95c0a5ac5
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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