Acetic Acid → HCID 67150767, compound

HRID 2056316Notes

Reaction equation

HRID 2056316 reaction equation
C[O:2][C:3](=[O:37])[CH2:4][CH2:5][CH:6]1[CH:13]2[CH:9]([O:10][CH:11]([CH:14]=[CH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12]2)[CH:8]([N:22]2[CH:30]=[N:29][C:28]3[C:23]2=[N:24][CH:25]=[N:26][C:27]=3[NH:31][C:32]([NH:34][CH2:35][CH3:36])=[O:33])[O:7]1.O.[OH-].[Li+].C(O)(=O)C>O1CCCC1>[CH2:35]([NH:34][C:32](=[O:33])[NH:31][C:27]1[N:26]=[CH:25][N:24]=[C:23]2[C:28]=1[N:29]=[CH:30][N:22]2[CH:8]1[CH:9]2[O:10][CH:11]([CH:14]=[CH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[O:12][CH:13]2[CH:6]([CH2:5][CH2:4][C:3]([OH:37])=[O:2])[O:7]1)[CH3:36]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 67150706HCID 67150706, compound

Product 1

HCID 67150767HCID 67150767, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-{6-[6-(3-Ethyl-ureido)-purin-9-yl]-2-styryl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-propionic acid methyl ester (5.0 g, 10 mmol) was dissolved in tetrahydrofuran (300 mL). Water (100 mL) was added, followed by lithium hydroxide (1.0 g, 25 mmol). The solution was allowed to stir 16 h at room temperature. It was acidified to pH 5 with acetic acid, concentrated in vacuo, then extracted with chloroform (300 mL). The organic extract was evaporated, redissolved in ethyl acetate and precipitated with heptane to afford the final product (3.9 g, 80%). 1H-NMR (300 MHz, d6 DMSO) δ 1.14 (t 3H, J=7 Hz), 1.90 (m, 2H), 2.19 (m, 2H), 3.26 (q, 2H, 3=6 Hz), 4.17 (m, 1H), 4.93 (ψt, 1H, J=6 Hz), 5.43 (dd, 1H, J=3 Hz, 7 Hz), 5.84 (d 1H, J=6 Hz), 6.24 (d, 1H, J=3 Hz), 6.28 (dd, 1H, J=7 Hz, 13 Hz), 6.90 (d, 1H, J 16 Hz), 7.35 (m, 3H), 7.51 (d, 2H, 3=7 Hz), 8.56 (s, 1H), 8.61 (s, 1H), 9.30 (t, 1H, 3=6 Hz).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with chloroform (300 mL)
  3. extractionThe organic extract
  4. customwas evaporated
  5. dissolutionredissolved in ethyl acetate
  6. customprecipitated with heptane

Sources & evidence

ORD record
ord-b45c14b6bb0e4911b5f3edcda7ea6676
Source dataset
uspto-grants-2008_02
Patent number
US07335648B2

Reaction notes

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