Water → HCID 42606275, compound

HRID 1617439Notes

Reaction equation

HRID 1617439 reaction equation
[OH-].[Na+:2].C([O:5][C:6](=[O:49])[CH2:7][CH2:8][CH2:9][NH:10][C@H:11]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:12][N:13]1[C:18](=[O:19])[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[C:21]=2[Cl:28])=[C:16]([CH3:29])[N:15]([CH2:30][C:31]2[C:36]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:34]=[CH:33][C:32]=2[F:41])[C:14]1=[O:42])C.O>CCO>[Na+:2].[Cl:28][C:21]1[C:22]([O:26][CH3:27])=[CH:23][CH:24]=[CH:25][C:20]=1[C:17]1[C:18](=[O:19])[N:13]([CH2:12][C@H:11]([NH:10][CH2:9][CH2:8][CH2:7][C:6]([O-:49])=[O:5])[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:14](=[O:42])[N:15]([CH2:30][C:31]2[C:36]([C:37]([F:40])([F:38])[F:39])=[CH:35][CH:34]=[CH:33][C:32]=2[F:41])[C:16]=1[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 67105708HCID 67105708, compound

Product 1

HCID 42606275HCID 42606275, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaOH (338 mL, 169 mmol, 0.5 M aq.) was added to a solution of 7d (103.9 g, 153.68 mol) in EtOH (472 mL) and the mixture was stirred for 2 hours. The EtOH was distilled off and water added to a total volume of 1080 mL (10.5 mL/g). This mixture was passed through a filter and washed with MIBK (600 mL×2). MIBK (700 mL) was added followed by NaOH (289 mL, 50% w/w) and extracted. The organic layer was separated and the aqueous extracted with MIBK (250 mL) and the combined organic layers washed with brine (500 mL), dried (NaSO4) and concentrated in vacuo to give a foam. This was lyophilized from 300 mL water to give 4-((R)-2-[5-(2-chloro-3-methoxy-phenyl)-3-(2-fluoro-6-trifluoromethyl-benzyl)-4-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethylamino)-butyric acid sodium salt 7-1 as an off white powder (92 g).

Workup

  1. distillationThe EtOH was distilled off
  2. additionwater added to a total volume of 1080 mL (10.5 mL/g)
  3. filtrationa filter
  4. washwashed with MIBK (600 mL×2)
  5. additionMIBK (700 mL) was added
  6. extractionextracted
  7. customThe organic layer was separated
  8. extractionthe aqueous extracted with MIBK (250 mL)
  9. washthe combined organic layers washed with brine (500 mL)
  10. dry with materialdried (NaSO4)
  11. concentrationconcentrated in vacuo
  12. customto give a foam

Sources & evidence

ORD record
ord-fdde49be03b74cd6bc428d62f87ce77f
Source dataset
uspto-grants-2014_07
Patent number
US08765948B2

Reaction notes

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