Hydrochloric Acid → HCID 86748043, compound

HRID 1741635Notes

Reaction equation

HRID 1741635 reaction equation
[OH:1][CH:2]([CH2:21][N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23][CH2:24][CH3:25])[CH2:3][O:4][CH:5]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7].[H-].[Na+].S(OC)(O[CH3:39])(=O)=O.Cl>CN(C=O)C>[CH3:39][O:1][CH:2]([CH2:21][N:22]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:23][CH2:24][CH3:25])[CH2:3][O:4][CH:5]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 86748044HCID 86748044, compound

Product 1

HCID 86748043HCID 86748043, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5 g. (11.3 mMol) 2-[2-hydroxy-3-(tert.-butyloxycarbonyl-propylamino)-propoxy]-3-phenyl-propiophenone are dissolved in 50 ml. abs. DMF and mixed at 0° C. with 0.30 g. (12.5 mMol) sodium hydride. Thereafter, it is stirred for 70 minutes at room temperature. Subsequently, the reaction mixture is cooled to 0° C. and a solution of 1.60 g. (12.5 mMol) dimethyl sulphate in 5 ml. absolute DMF added dropwise thereto. After 40 minutes at 0° to 5° C., the reaction mixture is emptied into 2N HCl. The phases are separated and the H2O phase extracted three times with CH2Cl2. The combined organic phases are after drying over Na2SO4, evaporated. There are obtained 4.5 g. of an orange oil which is purified column chromatographically. Column chromatography: silica gel, Bz:EE=14:1. The purified oil crystallises in a low-cooling cabinet.

Workup

  1. temperatureSubsequently, the reaction mixture is cooled to 0° C.
  2. waitAfter 40 minutes at 0° to 5° C.
  3. customThe phases are separated
  4. extractionthe H2O phase extracted three times with CH2Cl2
  5. dry with materialafter drying over Na2SO4
  6. customevaporated
  7. customThere are obtained 4.5 g
  8. customof an orange oil which is purified column chromatographically
  9. customThe purified oil crystallises in a low-cooling cabinet

Sources & evidence

ORD record
ord-c1413b33497f4fc2802b3a4331e8e64d
Source dataset
uspto-grants-1994_08
Patent number
US05334602

Reaction notes

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