Benzyl Alcohol → HCID 137194537, compound

HRID 494607Notes

Reaction equation

HRID 494607 reaction equation
[CH2:1](O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)[C:11]([OH:13])=[O:12].[NH2:16][C:17]1[CH:46]=[CH:45][C:20]2[NH:21][C:22]([C:27]3[C:28](=[O:44])[C:29]([CH2:41][CH2:42][CH3:43])([CH2:38][CH2:39][CH3:40])[C:30]4[C:35]([C:36]=3[OH:37])=[CH:34][CH:33]=[CH:32][CH:31]=4)=[N:23][S:24](=[O:26])(=[O:25])[C:19]=2[CH:18]=1.C(N(CC)CC)C>ClCCl.Cl>[OH:37][C:36]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH2:38][CH2:39][CH3:40])([CH2:41][CH2:42][CH3:43])[C:28](=[O:44])[C:27]=1[C:22]1[NH:21][C:20]2[CH:45]=[CH:46][C:17]([NH:16][S:24]([NH:23][C:11](=[O:12])[O:13][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)(=[O:26])=[O:25])=[CH:18][C:19]=2[S:24](=[O:26])(=[O:25])[N:23]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 136384804HCID 136384804, compound

Product 1

HCID 137194537HCID 137194537, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent3×

Procedure

A solution of chlorosulfonyl isocyante (25 mL, 0.281 mmol) in dichloromethane, was treated with benzyl alcohol (29 μL, 0.281 mmol) dropwise at room temp, stirred for 30 min, treated with a solution of example 71 (103 mg, 0.234 mmol) and triethylamine (130 μL, 0.936 mmol) in 3 mL of dichloromethane, stirred for 2 h, diluted with 10 mL of dichloromethane and 10 mL of 1N HCl. The organic phase was dried over Na2SO4, concentrated, and purified by silica gel chromatography with a gradient of methanol in dichloromethane (0-3%) to afford the desired product (26 mg, 17% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.59 (m, 2H) 0.68 (m, 6H) 0.91 (m, 2H) 2.01 (m, 2H) 2.18 (m, 2H) 5.11 (s, 2H) 7.50 (m, 11H) 8.17 (d, J=7.72 Hz, 1H) 10.04 (s, 1H) 11.10 (s, 1H) 12.13 (s, 1H) 13.74 (d, J=21.69 Hz, 1H); (ESI+) m/z 653 (M+H)+ (ESI+) m/z 670 (M+NH4)+ (ESI+) m/z 675 (M+Na)+ (ESI+) m/z 1327 (2M+Na)+ (ESI−) m/z 1303 (2M−H)− (ESI−) m/z 651 (M−H)−

Workup

  1. stirringstirred for 2 h
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography with a gradient of methanol in dichloromethane (0-3%)

Sources & evidence

ORD record
ord-8c95e1fc568841ef9444f0928e16de1a
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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