Water → HCID 58368464, compound

HRID 1192727Notes

Reaction equation

HRID 1192727 reaction equation
O[C@H]([C@@H](O)C(O)=O)C(O)=O.[Cl:11][C:12]1[CH:21]=[C:20]([C@@H:22]([NH2:24])[CH3:23])[C:19]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)=[C:18]2[C:13]=1[CH:14]=[CH:15][N:16]=[N:17]2.C(=O)([O-])[O-].[Na+].[Na+].O>C(Cl)Cl>[Cl:11][C:12]1[CH:21]=[C:20]([C@@H:22]([NH2:24])[CH3:23])[C:19]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=2)=[C:18]2[C:13]=1[CH:14]=[CH:15][N:16]=[N:17]2

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 67301025HCID 67301025, compound

Product 1

HCID 58368464HCID 58368464, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (2R,3R)-2,3-dihydroxysuccinic acid-(1S)-1-[5-chloro-8-(3-fluorophenyl)cinnolin-7-yl]ethanamine (0.75:1) (43 g, 103 mmol) in methylene chloride (570 mL) was treated with 2.0 M sodium carbonate in water (400 mL, 800 mmol) was added. The reaction mixture was treated with additional methylene chloride (400 mL) to dissolve the solid that had formed a ball. The methylene chloride solution was separated and concentrated to give the desired product (29 g, 94%) as an off-white solid. This material was used directly in the next step without further purification.

Workup

  1. additionwas added
  2. dissolutionto dissolve the solid
  3. customthat had formed a ball
  4. customThe methylene chloride solution was separated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d2c9811270464c6d8de62b12b8bef3db
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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