1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-[3-(3,4-Dihydro-5-hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-yl)-1-oxopropoxy]-2,5-pyrrolidinedione

HRID 399164Notes

Reaction equation

HRID 399164 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]([CH3:19])[CH: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].C(N=C=NCCCN(C)C)C>C(Cl)Cl>[OH:1][C:2]1[C:7]2[CH:8]([CH3:19])[CH: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 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 189701453,4-Dihydro-5-hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanoic acid

Product 1

HCID 189701411-[3-(3,4-Dihydro-5-hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-yl)-1-oxopropoxy]-2,5-pyrrolidinedioneYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 297 mg (0.88 mmol) of 3,4-Dihydro-5-hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-propanoic acid in 20 mL of anhy. CH2Cl2 under argon was added 246 mg (2.14 mmol) of N-hydroxysuccinimide (Aldrich) and the reaction stirred for 15 min. 408 mg (2.14 mmol) of 1-ethyl-3-(dimethylaminopropyl)carbodiimide (Sigma) was then added and the reaction stirred at RT for 3 hr. The reaction was diluted to five times the volume with CH2Cl2, washed with 0.1N aq. HCl that had been saturated with NaCl, followed by sat. aq. NaCl, followed by sat. aq. NaHCO3 (×3), dried and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with 1:1 EtOAc-CH2Cl2. The product fractions were combined and evaporated under reduced pressure and dried under high vacuum to give 297 mg (78%) of 1-[3-(3,4-Dihydro-5-hydroxy-2,2,4-trimethyl-7-pentyl-2H-1-benzopyran-3-yl)-1-oxopropoxy]-2,5-pyrrolidinedione as a white foam. HR (+) FAB MS: Calc (M+H), 432.2386; Observed, 432.2413.

Workup

  1. stirringthe reaction stirred at RT for 3 hr
  2. washwashed with 0.1N aq. HCl that
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with 1:1 EtOAc-CH2Cl2
  7. customevaporated under reduced pressure
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-95367b5dd3074a9e9d361d824470577a
Source dataset
uspto-grants-1998_10
Patent number
US05817766

Reaction notes

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