Water → HCID 11237832, compound

HRID 1454109Notes

Reaction equation

HRID 1454109 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C@@H:13]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[C:31]([O:32][CH3:33])=[CH:30][C:29]([CH2:34][O:35][CH2:36][CH3:37])=[CH:28][C:27]=2[O:38][CH3:39])=[CH:22][CH:21]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])O.[Na+].O.[F:46][C:47]1[CH:55]=[CH:54][CH:53]=[C:52]([F:56])[C:48]=1[C:49](Cl)=[O:50]>C(OCC)(=O)C>[F:46][C:47]1[CH:55]=[CH:54][CH:53]=[C:52]([F:56])[C:48]=1[C:49]([NH:12][C@@H:13]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[C:27]([O:38][CH3:39])=[CH:28][C:29]([CH2:34][O:35][CH2:36][CH3:37])=[CH:30][C:31]=2[O:32][CH3:33])=[CH:22][CH:21]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:50]

Participants

6

Reactant 4

HCID 962WaterHCID 874382,6-Difluorobenzoyl chlorideHCID 516892Sodium BicarbonateHCID 86599825HCID 86599825, compound

Product 1

HCID 11237832HCID 11237832, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ethyl (αS)-α-amino-4′-ethoxymethyl-2′,6′-dimethoxy(1,1′-biphenyl)-4-propionate p-toluenesulfonate (29.0 g), sodium hydrogen carbonate (15.2 g), water (290 ml) and ethyl acetate (290 ml) was added dropwise 2,6-difluorobenzoyl chloride (9.6 g) at 15° C. or below and the mixture was stirred for 30 minutes at the same temperature. The ethyl acetate layer was washed with saturated aqueous NaCl solution and dried over magnesium sulfate. The solvent was removed in vacuo. The residue was recrystallized from isopropanol-water to yield ethyl (αS)-α-[(2,6-difluorobenzoyl)amino]-4′-ethoxymethyl-2′,6′-dimethoxy(1,1′-biphenyl)-4-propionate (26.4 g).

Workup

  1. washThe ethyl acetate layer was washed with saturated aqueous NaCl solution
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed in vacuo
  4. customThe residue was recrystallized from isopropanol-water

Sources & evidence

ORD record
ord-fe7d8de7d2604f94ac1732c76aadd525
Source dataset
uspto-grants-2009_01
Patent number
US07476758B2

Reaction notes

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