Nitrogen → HCID 54537147, compound

HRID 326909Notes

Reaction equation

HRID 326909 reaction equation
CCN([CH2:6][CH3:7])CC.[CH3:8][S:9](Cl)(=O)=O.[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[CH:27]=1)O)(=[O:15])[CH3:14].C([O-])(O)=O.[Na+].S([O-])(=O)(=O)C.SCC(C)[C:53]([O:55][CH2:56][CH3:57])=[O:54].C([O-])([O-])=O.[Cs+].[Cs+].N#N>C(Cl)Cl.CC#N>[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH2:23][CH:24]([S:9][CH2:8][CH:6]([CH3:7])[C:53]([O:55][CH2:56][CH3:57])=[O:54])[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH2:32][O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][O:35]2)[CH:27]=1)(=[O:15])[CH3:14]

Participants

11

Reactant 8

HCID 947NitrogenHCID 8471TriethylamineHCID 10796Cesium carbonateHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 516892Sodium BicarbonateHCID 15289599Ethyl 3-mercapto-2-methylpropanoateHCID 53725555HCID 53725555, compound

Product 1

HCID 54537147HCID 54537147, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

At -40° C., Et3N (triethylamine) (1.60 mL, 11.5 mmol) and methanesulfonyl chloride (750 μl, 9.69 mmol) were added to a solution of the alcohol of Step 6 (7.39 mmol) in 74 mL of CH2Cl2 and the mixture was stirred at -40° C. for an hour and at -10° C. for 45 minutes. Saturated aq NaHCO3 was then added and the mesylate was extracted with CH2Cl2, dried over Na2SO4 and concentrated. To this mesylate in 150 mL of anhydrous CH3CN, ethyl 3-mercapto-2-methylpropanoate (Example 4, Step 6; 2.20 mL, approx. 15 mmol) and Cs2CO3 (7.57 g, 23.2 mmol) were added and the mixture was stirred under a stream of N2 for 2 hours. 25% Aq NH4OAc was then added and the title product was extracted with EtOAc, dried over Na2SO4 and purified by flash chromatography on silica with EtOAc:toluene.

Workup

  1. extractionthe mesylate was extracted with CH2Cl2
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. extractionthe title product was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. custompurified by flash chromatography on silica with EtOAc

Sources & evidence

ORD record
ord-2c41e1f9d5c04b79aedec6785c467dcc
Source dataset
uspto-grants-1993_12
Patent number
US05270324

Reaction notes

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