Benzyl Alcohol → HCID 137194538, compound

HRID 494609Notes

Reaction equation

HRID 494609 reaction equation
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[NH2:17][C:18]1[CH:47]=[CH:46][C:21]2[NH:22][C:23]([C:28]3[C:29](=[O:45])[C:30]([CH3:44])([CH2:39][CH2:40][CH:41]([CH3:43])[CH3:42])[C:31]4[C:36]([C:37]=3[OH:38])=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:24][S:25](=[O:27])(=[O:26])[C:20]=2[CH:19]=1.C(N(CC)CC)C>ClCCl>[CH2:8]([O:15][C:6](=[O:7])[NH:5][S:2]([NH:17][C:18]1[CH:47]=[CH:46][C:21]2[NH:22][C:23]([C:28]3[C:29](=[O:45])[C:30]([CH3:44])([CH2:39][CH2:40][CH:41]([CH3:43])[CH3:42])[C:31]4[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:37]=3[OH:38])=[N:24][S:25](=[O:27])(=[O:26])[C:20]=2[CH:19]=1)(=[O:4])=[O:3])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 136375607HCID 136375607, compound

Product 1

HCID 137194538HCID 137194538, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of chlorosulfonyl isocyanate (60 μL, 0.6 mmol) in 4 mL anhydrous dichloromethane at room temperature was treated drop wise with benzyl alcohol (60 uL, 0.6 mmol). After one hour, a solution of Example 34B (238 mg, 0.5 mmol), triethyl amine (300 μL, 2 mmol) in 2 mL dichloromethane, was added drop wise. The reaction was diluted with dichloromethane and extracted with 1 N HCl. The aqueous layer was extracted with dichloromethane and the combined organic layers dried with anhydrous MgSO4, concentrated and purified by chromatography to give the desired product (225 mg, 69%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42 (m, 1H) 0.69 (d, J=6.62 Hz, 3H) 0.72 (d, J=6.62 Hz, 3H) 0.81 (m, 1H) 1.32 (m, 1H) 1.58 (s, 3H) 2.08 (m, 1H) 2.23 (m, 1H) 5.11 (s, 2H) 7.30 (m, 6H) 7.47 (dd, J=9.01, 2.39 Hz, 1H) 7.54 (m, 1H) 7.62 (d, J=2.57 Hz, 1H) 7.70 (d, J=9.19 Hz, 1H) 7.77 (d, J=3.68 Hz, 2H) 8.17 (d, J=8.09 Hz, 1H) 11.12 (s, 1H) 12.15 (s, 1H) 13.78 (s, 1H). MS (ESI−) m/z=651 (M−H)−.

Workup

  1. extractionextracted with 1 N HCl
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialthe combined organic layers dried with anhydrous MgSO4
  4. concentrationconcentrated
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-baae54b23a8448fca9b24764f223729b
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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