Succinic anhydride → HCID 135968533, compound

HRID 1638724Notes

Reaction equation

HRID 1638724 reaction equation
[OH:1][C@@H:2]([CH2:17][OH:18])[CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2.[C:19]1(=[O:25])[O:24][C:22](=O)[CH2:21][CH2:20]1.C(N([CH2:31][CH3:32])CC)C>CN(C)C=O>[C:19]([CH2:20][CH2:31][CH2:32][O:1][C@@H:2]([CH2:17][O:18][CH2:22][CH2:21][CH2:20][C:19]([OH:24])=[O:25])[CH2:3][O:4][CH2:5][N:6]1[CH:14]=[N:13][C:12]2[C:11](=[O:15])[NH:10][C:9]([NH2:16])=[N:8][C:7]1=2)([OH:25])=[O:24]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8471TriethylamineHCID 135446903HCID 135446903, compound

Product 1

HCID 135968533HCID 135968533, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-9-(2,3-dihydroxy-1propoxymethyl)guanine (1.37 g, 5 mmol), 2.0 g of succinic anhydride, and 2.8 ml of anhydrous triethylamine in dry dimethylformamide (75 ml) is heated in an oil bath at 60° . When the reaction is complete (24 hours) the mixture is cooled and evaporated to dryness in vacuo. The residue is resuspended in ice-water (50 ml) and the pH is adjusted to 2 with 2N-HCl. The precipitate is filtered, thoroughly washed with ice-water, and dried in vacuo. The precipitate is then recrystallized from methanol.

Workup

  1. custom(24 hours)
  2. temperatureis cooled
  3. customevaporated to dryness in vacuo
  4. filtrationThe precipitate is filtered
  5. washthoroughly washed with ice-water
  6. customdried in vacuo
  7. customThe precipitate is then recrystallized from methanol

Sources & evidence

ORD record
ord-687ee0e6045f4db894280ffeef48da74
Source dataset
uspto-grants-1989_11
Patent number
US04880820

Reaction notes

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