Triethylamine → HCID 67089257, compound

HRID 2075627Notes

Reaction equation

HRID 2075627 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:22])[O:7][CH2:8][CH:9]1[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2.[C:23](O)(=[O:31])[C@@H:24]([C@H:26]([C:28]([OH:30])=[O:29])[OH:27])[OH:25].C(N(CC)CC)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[CH:11]1[C:10]2[CH:9]([CH2:8][O:7][C:6]([NH:5][CH2:4][CH2:3][NH:2][C:23](=[O:31])[CH:24]([OH:25])[CH:26]([OH:27])[C:28]([OH:30])=[O:29])=[O:22])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 444305L-Tartaric acid2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 2818106(9H-fluoren-9-yl)methyl N-(2-aminoethyl)carbamate hydrochloride2×

Product 1

HCID 67089257HCID 67089257, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

9H-9-fluorenylmethyl N-(2-aminoethyl)carbamate hydrochloride (Compound 14; 5.00 g, 153.7 mmol) and L-(+)-tartaric acid (Compound 15; 5.89 g, 39.2 mmol) were dissolved by the addition of N,N-dimethylformamide (300 ml) and triethylamine (5.46 ml, 39.2 mmol). Next, 1-hydroxybenzotriazol hydrate (2.52 g, 16.5 mmol) was added, a solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.16 g, 16.5 mmol) in N,N-dimethylformamide (200 ml) was added drop by drop, and this was followed by overnight stirring at room temperature. This was concentrated under reduced pressure, the residue obtained was dissolved in ethyl acetate, and the organic phase was washed with a 2N aqueous solution of citric acid. Next, reverse extraction was conducted using aqueous sodium hydrogen carbonate, after which the water phase obtained was washed with ethyl acetate. Under ice cooling, the water phase was rendered acidic with a 2N aqueous solution of citric acid, after which it was extracted with ethyl acetate. The organic phase was washed with saturated brine, after which it was dried with sodium sulfate. After the solid was filtered and concentrated under reduced pressure, crystallization from methanol-diethyl ether was conducted to yield the desired N-[2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-2,3-dihydroxy-succinamic acid (2.72 g, 42%).

Workup

  1. concentrationThis was concentrated under reduced pressure
  2. customthe residue obtained
  3. washthe organic phase was washed with a 2N aqueous solution of citric acid
  4. extractionextraction
  5. customafter which the water phase obtained
  6. washwas washed with ethyl acetate
  7. extractionafter which it was extracted with ethyl acetate
  8. washThe organic phase was washed with saturated brine
  9. dry with materialafter which it was dried with sodium sulfate
  10. filtrationAfter the solid was filtered
  11. concentrationconcentrated under reduced pressure, crystallization from methanol-diethyl ether

Sources & evidence

ORD record
ord-d15319ad9ec64f75a3e924d6ebd571c9
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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