Methanol → HCID 11547193, compound

HRID 1174533Notes

Reaction equation

HRID 1174533 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]([C@@H:27]2[C@H:32]([NH:33][C:34](=O)[C:35]3[CH:49]=[CH:48][C:38]([C:39]([N:41]([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])=[O:40])=[CH:37][CH:36]=3)[CH2:31][CH2:30][O:29][CH2:28]2)[CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH3:17].CO.C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[CH2:16]([O:18][C:19]1[CH:20]=[C:21]2[C:22](=[CH:23][C:24]=1[O:25][CH3:26])[C:34]([C:35]1[CH:49]=[CH:48][C:38]([C:39]([N:41]([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])=[O:40])=[CH:37][CH:36]=1)=[N:33][C@H:32]1[C@@H:27]2[CH2:28][O:29][CH2:30][CH2:31]1)[CH3:17]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 59006937HCID 59006937, compound

Product 1

HCID 11547193HCID 11547193, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

Alternatively a solution of 12.5 mmol of trifluoromethanesulfonic anhydride dissolved in 10 ml dichloromethane is added over a period of 20 min to a cooled (ice-water bath) solution of 2.5 mmol of N-[(3R,4R)-3-(3-Ethoxy-4-methoxy-phenyl)-tetrahydro-pyran-4-yl]-N′,N′-diisopropyl-terephthalamide and 7.5 mmol of 4-dimethylamino-pyridine in 30 ml of dichloromethane. The solution is stirred over night and then added to a cooled (ice-water bath) mixture of 10 ml of methanol, 10 ml of triethyl amine and 20 ml of dichloromethane and the mixture is stirred for 1 h. After concentration under reduced pressure the solid residue is purified by column chromatography on SiO2 (di-isopropylether/methanol/triethyl amine 18/1/1 vol/vol/vol), the main product fraction is separated and concentrated yielding the title compound as grayish solid foam. M.p. 98-102° C. (unsharp, enamel-like shrinking starting at about 88° C.)

Workup

  1. additionis added over a period of 20 min to
  2. additionadded to
  3. temperaturea cooled
  4. stirringthe mixture is stirred for 1 h
  5. concentrationAfter concentration under reduced pressure the solid residue
  6. customis purified by column chromatography on SiO2 (di-isopropylether/methanol/triethyl amine 18/1/1 vol/vol/vol)
  7. customthe main product fraction is separated
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-71db5bb5e2b440e79fc11922d7e6f061
Source dataset
uspto-grants-2010_11
Patent number
US07838521B2

Reaction notes

Loading…