Sodium Hydroxide → HCID 18767732, compound

HRID 480123Notes

Reaction equation

HRID 480123 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH2:5][C:6]12[CH2:13][C:10]([C:14]3[NH:22][C:21]4[C:20](=[O:23])[N:19]([CH2:24][CH2:25][CH3:26])[C:18](=[O:27])[N:17]([CH2:28][CH2:29][CH3:30])[C:16]=4[N:15]=3)([CH2:11][CH2:12]1)[CH2:9][CH2:8][CH2:7]2.[OH-].[Na+]>C1COCC1>[O:27]=[C:18]1[N:17]([CH2:28][CH2:29][CH3:30])[C:16]2[N:15]=[C:14]([C:10]34[CH2:13][C:6]([CH2:5][CH2:4][C:3]([OH:31])=[O:2])([CH2:12][CH2:11]3)[CH2:7][CH2:8][CH2:9]4)[NH:22][C:21]=2[C:20](=[O:23])[N:19]1[CH2:24][CH2:25][CH3:26]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67079140HCID 67079140, compound

Product 1

HCID 18767732HCID 18767732, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[5-(2,6-dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-bicyclo-[3.2.1]oct-1-yl]-propionic acid methyl ester (0.456 mmol, 0.196 g) in THF (10 ml) was treated with 20% NaOH (2 ml) and stirred overnight at RT. The reaction was concentrated to remove the THF. The aqueous residue was acidified (pH 2-3) with conc. HCl and iPrOH was added to homogeneity. The solution was concentrated on the rotovap until solids just began to separate. After chilling in ice 1 h, the precipitated solids were collected by vacuum filtration, rinsed with a little H2O and chased with Et2O. The solids were dried on the filter to provide the desired product (0.061 g, 32%). 13C NMR (100 MHz, CDCl3): 11.11 (q), 11.26 (q), 20.04 (t), 21.25 (t), 21.31 (t), 29.51 (s), 33.97 (t), 35.15 (s), 36.16 (t), 36.39 (t), 43.32 (t), 43.41 (t), 45.38 (t), 49.18 (t), 106.01 (s), 149.40 (s), 150.90 (s), 156.30 (s), 161.56 (s), 178.54 (s).

Workup

  1. concentrationThe reaction was concentrated
  2. customto remove the THF
  3. additionwas added to homogeneity
  4. concentrationThe solution was concentrated on the rotovap until solids
  5. customto separate
  6. temperatureAfter chilling in ice 1 h
  7. filtrationthe precipitated solids were collected by vacuum filtration
  8. washrinsed with a little H2O and chased with Et2O
  9. customThe solids were dried on the
  10. filtrationfilter

Sources & evidence

ORD record
ord-75f26715d13f4858b2395108aad833fa
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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