Hydrochloric Acid → HCID 59712482, compound

HRID 2222442Notes

Reaction equation

HRID 2222442 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:15]([OH:25])[C:16]2([C:21]([O:23][CH3:24])=[O:22])[CH2:20][CH2:19][CH2:18][O:17]2)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].N1C=CC=CC=1.Cl>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:26]([O:25][CH:15]([C:13]1[CH:12]=[CH:11][N:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:14]=1)[C:16]1([C:21]([O:23][CH3:24])=[O:22])[CH2:20][CH2:19][CH2:18][O:17]1)(=[O:28])[CH3:27]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 59712337HCID 59712337, compound

Product 1

HCID 59712482HCID 59712482, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4.23 g of methyl 2-[[2-(benzyloxy)-4-pyridyl](hydroxy)methyl]tetrahydro-2-furancarboxylate in 20 ml of dichloromethane were added 5 ml of acetic anhydride, 5 ml of pyridine and 0.43 g of 4-dimethylaminopyridine, and the mixture was stirred at room temperature for 15 hours. 300 ml of ethyl acetate and 100 ml of hydrochloric acid (2N) were added thereto. The organic layer was sequentially washed with 100 ml of water, 100 ml of saturated aqueous sodium hydrogencarbonate and 100 ml of brine, dried over magnesium sulfate and evaporated, to give 4.52 g of the title compound as a colorless oil.

Workup

  1. washThe organic layer was sequentially washed with 100 ml of water, 100 ml of saturated aqueous sodium hydrogencarbonate and 100 ml of brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-6c6eef613e63463390698c0a39c42b7f
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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