2,3-Dihydroxybutanedioic Acid → HCID 67772440, compound

HRID 1808819Notes

Reaction equation

HRID 1808819 reaction equation
[N:1]1([CH2:5][C@@H:6]([N:10]([CH3:20])[C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH:7]([CH3:9])[CH3:8])[CH2:4][CH2:3][CH2:2]1.[C:21]([OH:30])(=[O:29])[CH:22]([CH:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23]>CC#N.O>[OH:25][CH:24]([CH:22]([OH:23])[C:21]([O-:30])=[O:29])[C:26]([O-:28])=[O:27].[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]([N:10]([C@@H:6]([CH:7]([CH3:8])[CH3:9])[CH2:5][NH+:1]2[CH2:4][CH2:3][CH2:2]2)[CH3:20])=[O:19])=[CH:17][CH:16]=1.[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]([N:10]([C@@H:6]([CH:7]([CH3:8])[CH3:9])[CH2:5][NH+:1]2[CH2:4][CH2:3][CH2:2]2)[CH3:20])=[O:19])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 67772438HCID 67772438, compound

Product 1

HCID 67772440HCID 67772440, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The title compound of Example 5.1 A was dissolved in MeCN (10 mL) and a solution of DL-tartaric acid (659 mg, 4.39 mmol) in water (15 mL) was added. The resulting mixture was filtered and the solution freeze dried in vacuo to give the title product (3.13 g, 66%). Mixture of rotamers: 1H NMR (400 MHz, DMSO-d6) δ 0.42-1.25, 1.52-1.86, 1.86-2.01, 2.01-2.24, 2.5-2.54, 2.64, 2.77, 2.84-3.23, 3.40-3.82, 3.95, 4.10-4.35, 7.10-7.71. Ratio major:minor:6:4. The compound was found to be amorphous by XRPD.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customthe solution freeze dried in vacuo

Sources & evidence

ORD record
ord-81f6940a7eb04b8ba3389a06475584a1
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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