Pivaloyl chloride → HCID 86588177, compound

HRID 1839237Notes

Reaction equation

HRID 1839237 reaction equation
C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[N:19]=[C:18]2[C:14]([N:15]=[CH:16][N:17]2[C@H:20]2[C@@H:24]3[O:25][C:26]([CH3:29])([CH3:28])[O:27][C@@H:23]3[C@@H:22]([C:30](O)=[O:31])[O:21]2)=[C:13]([NH:33][CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[N:12]=1.C(Cl)(=O)C(C)(C)C.[CH3:47][C:48]([CH3:54])([CH3:53])[C:49]([NH:51][NH2:52])=[O:50]>O1CCCC1>[CH3:47][C:48]([CH3:54])([CH3:53])[C:49]([NH:51][NH:52][C:30]([C@@H:22]1[C@@H:23]2[C@@H:24]([O:25][C:26]([CH3:28])([CH3:29])[O:27]2)[C@H:20]([N:17]2[CH:16]=[N:15][C:14]3[C:18]2=[N:19][C:11]([Cl:10])=[N:12][C:13]=3[NH:33][CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[O:21]1)=[O:31])=[O:50]

Participants

6

Reactant 4

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 5451472,2-DimethylpropanehydrazideHCID 18336832HCID 18336832, compound

Product 1

HCID 86588177HCID 86588177, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Diisopropylethylamine (0.487 ml) was added to a stirred solution of (3aS,4S,6R,6aR)-6-[2-chloro-6-(tetrahydro-pyran-4-ylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid (350 mg) in dry tetrahydrofuran (8 ml) at 0° C. under nitrogen. After 5 min pivaloyl chloride (0.098 ml) was added and the mixture was stirred at 0° C. for 2.5 h. 2,2-Dimethyl-propionic acid hydrazide was added in tetrahydrofuran (2 ml) at 0°, and stirring was continued at 0-22° C. overnight. The mixture was concentrated in vacuo and partitioned between ethyl acetate (2×30 ml) and saturated aqueous sodium bicarbonate (30 ml). The organic layers were washed with brine (50 ml), dried (MgSO4) and evaporated in vacuo. The residue was azeotroped with dichloromethane (10 ml) to give the title compound as a cream solid (357 mg).

Workup

  1. stirringstirring
  2. waitwas continued at 0-22° C. overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. custompartitioned between ethyl acetate (2×30 ml) and saturated aqueous sodium bicarbonate (30 ml)
  5. washThe organic layers were washed with brine (50 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was azeotroped with dichloromethane (10 ml)

Sources & evidence

ORD record
ord-230c2055f9ce40b597b829c3338b18ef
Source dataset
uspto-grants-2004_01
Patent number
US06677316B2

Reaction notes

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