Sodium Carbonate → methyl N-[(4'-amino-1,1'-biphenyl-4-yl)sulfonyl]-N-methyl-D-valinate

HRID 29315Notes

Reaction equation

HRID 29315 reaction equation
[CH3:1][N:2]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C@@H:3]([C:7]([O:9][CH3:10])=[O:8])[CH:4]([CH3:6])[CH3:5].O.O.[Sn](Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]2[CH:16]=[CH:15][C:14]([S:11]([N:2]([CH3:1])[C@@H:3]([C:7]([O:9][CH3:10])=[O:8])[CH:4]([CH3:6])[CH3:5])(=[O:13])=[O:12])=[CH:19][CH:18]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 61436Stannous chloride dihydrateHCID 68712541HCID 68712541, compound

Product 1

HCID 59150916methyl N-[(4'-amino-1,1'-biphenyl-4-yl)sulfonyl]-N-methyl-D-valinateYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 0.22 g of methyl N-methyl-N-[(4′-nitro-1,1′-biphenyl-4-yl)sulfonyl]-D-valinate in 8 mL of ethyl acetate was added 1.21 g of tin (II) chloride dihydrate and the reaction was stirred at room temperature overnight. To the reaction was added ˜8 mL of 2N sodium carbonate to adjust the pH to ˜8-9. The reaction was then filtered through celite. The filtrate washed with water and brine, dried over Na2SO4, filtered, and concentrated to provide 0.19 g of as methyl N-[(4′-amino-1,1′-biphenyl-4-yl)sulfonyl]-N-methyl-D-valinate as an oil. Yield 95%. MS:377.2 (M+H)+.

Workup

  1. filtrationThe reaction was then filtered through celite
  2. washThe filtrate washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c5ce4e3c5bbc4839a98d0b5a0b4546bb
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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