5-Aminovaleric acid → HCID 42610633, compound

HRID 539441Notes

Reaction equation

HRID 539441 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].C1C(=O)N([O:16][C:17]([C:19]2[C:24]([F:25])=[C:23]([F:26])[C:22]([N:27]=[N+:28]=[N-:29])=[C:21]([F:30])[C:20]=2[F:31])=O)C(=O)C1.Cl>CS(C)=O>[N:27]([C:22]1[C:21]([F:30])=[C:20]([F:31])[C:19]([C:17]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7])=[O:16])=[C:24]([F:25])[C:23]=1[F:26])=[N+:28]=[N-:29]

Participants

5

Reactant 3

HCID 1385-Aminovaleric acidHCID 313Hydrochloric AcidHCID 27625791-[(4-Azido-2,3,5,6-tetrafluorobenzoyl)oxy]pyrrolidine-2,5-dione

Product 1

HCID 42610633HCID 42610633, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-aminovaleric acid (12 mg, 100 μmol) in dry DMSO (250 μL) was added N-succinimidyl 4-azido-2,3,5,6-tetrafluorobenzoate (25 mg, 75 μmol). The reaction was allowed to proceed overnight at 45° C. in the dark. The mixture was then acidified with 250 μL of 0.5 N hydrochloric acid and extracted with 400 μL of ethyl acetate three times. The combined extracts were concentrated in vacuo and purified by silica chromatography using 2:1 hexane-ethyl acetate to yield the desired product as a white powder. Yielded: 3 mg, 9 μmol, 12%. TLC: Rf=0.3 (1:1 hexane-ethyl acetate) 1H-NMR (300 MHz, (CD3)2SO): δ 12.03 (s, 1H), 8.89 (t, 1H, J=5.4), 3.23 (q, 2H, J=6.3), 2.22 (t, 2H, 0.1=7.2), 1.497 (m, 4H). ESI-MS m/z: (neg) 333.07 [M−H]−. Calc. 334.23

Workup

  1. extractionextracted with 400 μL of ethyl acetate three times
  2. concentrationThe combined extracts were concentrated in vacuo
  3. custompurified by silica chromatography

Sources & evidence

ORD record
ord-106072870672490498e4816689538c65
Source dataset
uspto-grants-2014_10
Patent number
US08871456B2

Reaction notes

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