D-Tartaric acid → HCID 86640697, compound

HRID 2176151Notes

Reaction equation

HRID 2176151 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]3[CH:16]=[CH:15][C:14]([F:18])=[CH:13][C:12]=3[C:11]3[CH2:19][N:20]4[CH2:25][CH2:24][CH:23]([C:10]2=3)[CH2:22][CH2:21]4)=[CH:4][CH:3]=1.[OH:26][C@@H:27]([C@H:31]([OH:35])[C:32]([OH:34])=[O:33])[C:28]([OH:30])=[O:29]>C(OCC)(=O)C.C(O)C.CO>[C:28]([CH:27]([CH:31]([C:32]([OH:34])=[O:33])[OH:35])[OH:26])([OH:30])=[O:29].[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]3[CH:16]=[CH:15][C:14]([F:18])=[CH:13][C:12]=3[C:11]3[CH2:19][N:20]4[CH2:21][CH2:22][CH:23]([C:10]2=3)[CH2:24][CH2:25]4)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 439655D-Tartaric acidHCID 45380480HCID 45380480, compound

Product 1

HCID 86640697HCID 86640697, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

The salt was prepared by dissolving the starting material from Example 164C (275. mg, 0.775 mmol) in ethyl acetate (5.0 mL) and ethanol (1.0 mL) then adding (2S,3S)-2,3-dihydroxysuccinic acid (128 mg, 0.852 mmol, dissolved in a minimal amount of methanol) slowly and stirring rapidly over night. The material precipitated to give a white solid. The solid was collected by filtration and dried under vacuum to give the titled compound: 1H NMR (300 MHz, methanol-d4) δ ppm 1.97-2.13 (m, 2H) 2.19-2.37 (m, 2H) 3.38-3.51 (m, 3H) 3.51-3.69 (m, 2H) 4.41 (s, 2H) 4.70 (s, 2H) 5.54 (s, 2H) 6.89-7.05 (m, 1H) 7.18 (dd, J=9.32, 2.58 Hz, 1H) 7.32-7.50 (m, 3H) 8.05 (s, 1H); MS (DCI/NH3) m/z 356 (M+H)+. Anal. Calcd. for C20H19ClFN3.C4H6O6: C, 56.98; H, 4.97; 8.31. Found: C, 56.71; H, 4.88; N, 8.20.

Workup

  1. customThe salt was prepared
  2. customThe material precipitated
  3. customto give a white solid
  4. filtrationThe solid was collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6817c690223540aaab2d42f04eb7edc1
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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