N-Hydroxysuccinimide → 1-[3-(5-Hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-yl)-1-oxopropoxy]-2,5-pyrrolidinedione

HRID 399158Notes

Reaction equation

HRID 399158 reaction equation
[OH:1][C:2]1[C:7]2[C:8]([CH3:19])=[C:9]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=[C:4]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:3]=1.O[N:26]1[C:30](=[O:31])[CH2:29][CH2:28][C:27]1=[O:32].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[OH:1][C:2]1[C:7]2[C:8]([CH3:19])=[C:9]([CH2:14][CH2:15][C:16](=[O:18])[O:17][N:26]3[C:30](=[O:31])[CH2:29][CH2:28][C:27]3=[O:32])[C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=[C:4]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:3]=1

Participants

5

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 189701435-Hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanoic acid

Product 1

HCID 189701331-[3-(5-Hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-yl)-1-oxopropoxy]-2,5-pyrrolidinedioneYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6 mg (0.018 mmol) of the acid 5-Hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanoic acid in anhy. methylene chloride under argon was added 10.3 mg (5 eq.) of N-hydroxysuccinimide (NHS) (Aldrich) followed by 8.6 mg (2.5 eq.) of 1-ethyl-3-(dimethylaminopropyl)carbodiimide hydrochloride (EDC.HCl) (Sigma). After stirring at RT under argon for 4 hr TLC indicated only traces of starting material were left. The reaction mixture was directly subjected to chromatography on silica gel plates, eluting with 50% EtOAc-hexane. The product band was isolated, washed with a little EtOAc, the washings stripped of solvent under reduced pressure and the residue dried under high vacuum to give 5 mg (65%) of 1-[3-(5-Hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-yl)-1-oxopropoxy]-2,5-pyrrolidinedione as a foam. HR (+) FAB MS: Calc (M+H), 430.2230; Observed, 430.2266.

Workup

  1. waitwere left
  2. washeluting with 50% EtOAc-hexane
  3. customThe product band was isolated
  4. washwashed with a little EtOAc
  5. customthe residue dried under high vacuum

Sources & evidence

ORD record
ord-fdcad16ed2f34ed08ec18393d0ace015
Source dataset
uspto-grants-1998_10
Patent number
US05817766

Reaction notes

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