Acetic Acid → HCID 67923326, compound

HRID 1084434Notes

Reaction equation

HRID 1084434 reaction equation
[Si]([O:8][C@@H:9]1[CH2:14][C@@H:13](/[CH:15]=[CH:16]/[C:17]2[N:18]([CH:35]([CH3:37])[CH3:36])[C:19](=[O:34])[C:20]3[C:25]([C:26]=2[C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:12][C@H:11]([O:38]C)[CH2:10]1)(C(C)(C)C)(C)C.C(O)(=O)C.O1CCCC1.O>C(OCC)C>[OH:38][CH:11]1[CH2:10][C@H:9]([OH:8])[CH2:14][C@@H:13](/[CH:15]=[CH:16]/[C:17]2[N:18]([CH:35]([CH3:37])[CH3:36])[C:19](=[O:34])[C:20]3[C:25]([C:26]=2[C:27]2[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=2)=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:12]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 67923398HCID 67923398, compound

Product 1

HCID 67923326HCID 67923326, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
70 °C

Procedure

A solution of (2S,4R,6S)-(E)-4-(t-butyldimethylsilyloxy)-6-[2-{4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl}ethen-1-yl]-2-methoxy-3,4,5,6-tetrahydro-2H-pyran [149 mg; prepared as described in Example 8(a)] in a mixture of glacial acetic acid, tetrahydrofuran and water (3:2:2 by volume; 5 ml) was stirred at 70° C. under argon and under a reflux condenser for 3 hours. The resulting clear solution was diluted with diethyl ether (50 ml), washed with water (20 ml) and then with saturated aqueous sodium bicarbonate solution (2×20 ml), dried over magnesium sulphate and evaporated. The resulting residue was subjected to flash chromatography on silica gel, using as eluant ethyl acetate containing from 0 to 50% hexane by volume, to give (2RS,4R,6S)-(E)-2,4-dihydroxy-6-[2-{4-(4-fluorophenyl)-2-isopropyl-1-oxo-1,2-dihydroisoquinolin-3-yl}-ethen-1-yl]-3,4,5,6-tetrahydro-2H-pyran (78 mg) in the form of a white foam.

Workup

  1. washwashed with water (20 ml)
  2. dry with materialwith saturated aqueous sodium bicarbonate solution (2×20 ml), dried over magnesium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-5a79eb4e793b49b3a4908701589ae70c
Source dataset
uspto-grants-1991_04
Patent number
US05004747

Reaction notes

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