Hydrochloric Acid → HCID 86752469, compound

HRID 1600074Notes

Reaction equation

HRID 1600074 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:34])[C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17](=[O:33])[CH2:18][C@H:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]2[NH:25]C(OC(C)(C)C)=O)=[CH:5][CH:4]=1)#[N:2].Cl.C(N(CC)CC)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>C(OCC)(=O)C.ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:34])[C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17](=[O:33])[CH2:18][C@H:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]2[NH:25][S:44]([CH3:43])(=[O:46])=[O:45])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70099875HCID 70099875, compound

Product 1

HCID 86752469HCID 86752469, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound (26.7 g, 57 mmol) obtained in the item (c) inchloroform (50 ml), a 4-N hydrochloride in ethyl acetate (30 ml) is added at 0° C. The mixture is stirred for 3 hours and then the solvent isevaporated. The resulting residue was dissolved in dichloromethane (250 ml)and triethylamine (19 ml) is added. Then, a solution of methanesulfonyl chloride (7.9 g, 68 mmol) in dichloromethane (50 ml) is added at 0°C. and the mixture is stirred for 3 hours. The organic layer is washed oncewith a saturated sodium bicarbonate solution, water and saturated brine, successively, and then dried over sodium sulfate. The resulting residue ispurified with silica gel chromatography (hexane-ethyl acetate) to give 18.6g of the titled compound (73%).

Workup

  1. stirringthe mixture is stirred for 3 hours
  2. washThe organic layer is washed oncewith a saturated sodium bicarbonate solution, water and saturated brine
  3. dry with materialsuccessively, and then dried over sodium sulfate

Sources & evidence

ORD record
ord-0c3ac8a6926d4424ac6bc696540546ed
Source dataset
uspto-grants-1998_04
Patent number
US05744487

Reaction notes

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