Diisopropylethylamine → HCID 67089528, compound

HRID 2075645Notes

Reaction equation

HRID 2075645 reaction equation
Cl.[CH:2]1[C:14]2[CH:13]([CH2:15][O:16][C:17]([NH:19][NH2:20])=[O:18])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:21](O)(=[O:29])[C@@H:22]([C@H:24]([C:26]([OH:28])=[O:27])[OH:25])[OH:23].C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+].S([O-])(O)(=O)=O.[K+]>C(OCC)C.CN(C)C=O>[CH:11]1[C:12]2[CH:13]([CH2:15][O:16][C:17]([NH:19][NH:20][C:21](=[O:29])[CH:22]([OH:23])[CH:24]([OH:25])[C:26]([OH:28])=[O:27])=[O:18])[C:14]3[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

9

Reactant 6

HCID 81531DiisopropylethylamineHCID 444305L-Tartaric acid2×HCID 516892Sodium BicarbonateHCID 516920Potassium bisulfateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23080809HCID 23080809, compound2×

Product 1

HCID 67089528HCID 67089528, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

N-(9H-9-fluorenylmethoxycarbonyl)hydrazine hydrochloride (Compound 40; 500 mg, 1.72 mmol) and L-(+)-tartaric acid (Compound 15; 634 mg, 4.22 mmol) were dissolved by the addition of N,N-dimethylformamide (10 ml) and diisopropylethylamine (300 μl, 1.72 mmol). Next, 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (485 mg, 2.53 mmol) was added, and this was followed by overnight stirring at room temperature. This was concentrated under reduced pressure; to the residue obtained, aqueous sodium hydrogen carbonate and diethyl ether were added; two liquid phases were separated. The water phase obtained was acidified with a 2N aqueous solution of potassium hydrogen sulfate under ice cooling, after which it was extracted with ethyl acetate. The organic phase was washed with saturated brine, after which it was dried with sodium sulfate. The solid was filtered and concentrated under reduced pressure, after which it was crystallized from methanol-diethyl ether to yield the desired 4-[N′-(9H-fluoren-9-ylmethoxycarbonyl)-hydrazino]-2,3-dihydroxy-4-oxo-butanoic acid (Compound 41: 413 mg, 63%).

Workup

  1. concentrationThis was concentrated under reduced pressure
  2. customto the residue obtained
  3. customtwo liquid phases were separated
  4. customThe water phase obtained
  5. extractionafter which it was extracted with ethyl acetate
  6. washThe organic phase was washed with saturated brine
  7. dry with materialafter which it was dried with sodium sulfate
  8. filtrationThe solid was filtered
  9. concentrationconcentrated under reduced pressure
  10. customafter which it was crystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-68f7bc37cd564c54b2ce1823e638ee71
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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