Succinic anhydride → HCID 18703948, compound

HRID 2288070Notes

Reaction equation

HRID 2288070 reaction equation
[OH:1][CH:2]1[CH:9]2[CH:5]3[O:6][C:7]([O:12][CH2:13][C:14]45[CH:25]6[CH2:26][C:21]([CH:33]=[O:34])([C:22]4([C:30]([OH:32])=[O:31])[C:23]([CH:27]([CH3:29])[CH3:28])=[CH:24]6)[CH:20]4[CH:16]([CH:17]([CH3:35])[CH2:18][CH2:19]4)[CH2:15]5)([CH:10]([OH:11])[CH:3]1[O:4]3)[O:8]2.[C:36]1(=[O:42])[O:41][C:39](=[O:40])[CH2:38][CH2:37]1>N1C=CC=CC=1>[C:39]([CH2:38][CH2:37][C:36]([O:1][CH:2]1[CH:9]2[CH:5]3[O:6][C:7]([O:12][CH2:13][C:14]45[CH:25]6[CH2:26][C:21]([CH:33]=[O:34])([C:22]4([C:30]([OH:32])=[O:31])[C:23]([CH:27]([CH3:29])[CH3:28])=[CH:24]6)[CH:20]4[CH:16]([CH:17]([CH3:35])[CH2:18][CH2:19]4)[CH2:15]5)([CH:10]([OH:11])[CH:3]1[O:4]3)[O:8]2)=[O:42])([OH:41])=[O:40]

Participants

4

Reactant 2

HCID 7922Succinic anhydride2×HCID 15459982HCID 15459982, compound

Product 1

HCID 18703948HCID 18703948, compoundYield 16.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20 mg of compound (2) was dissolved in 1.0 ml of pyridine and stirred together with 16.4 mg of succinic anhydride at room temperature. After 52 hours, 8.2 mg of succinic anhydride was added, and the reaction was conducted for another 20 hours. The reaction solution was concentrated in vacuo and subjected to reversed phase chromatography (Capcell Pak C18 UG-120, Shiseido, 2.0φ×25 cm, 0.05% trifluoroacetic acid-acetonitrile [6:4], flow rate 10.0 ml/min, detection 210 nm) for purification, and the desired fraction was recovered. The recovered fraction was poured into 100 ml of 0.1 M sodium phosphate buffer pH 5.5 and extracted with 100 ml of ethyl acetate. The ethyl acetate extract was concentrated in vacuo to give 4.0 mg of compound (20).

Workup

  1. waitthe reaction was conducted for another 20 hours
  2. concentrationThe reaction solution was concentrated in vacuo
  3. customsubjected to reversed phase chromatography (Capcell Pak C18 UG-120, Shiseido, 2.0φ×25 cm, 0.05% trifluoroacetic acid-acetonitrile [6:4], flow rate 10.0 ml/min, detection 210 nm) for purification
  4. customthe desired fraction was recovered
  5. additionThe recovered fraction was poured into 100 ml of 0.1 M sodium phosphate buffer pH 5.5
  6. extractionextracted with 100 ml of ethyl acetate
  7. extractionThe ethyl acetate extract
  8. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-b72100565b2042adab38721ce0c567d7
Source dataset
uspto-grants-2000_07
Patent number
US06087390

Reaction notes

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