Benzyl Alcohol → HCID 136347220, compound

HRID 601427Notes

Reaction equation

HRID 601427 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.[NH2:16][C:17]1[CH:45]=[CH:44][C:20]2[NH:21][C:22]([C:27]3[C:28](=[O:43])[N:29]([NH:38][CH:39]4[CH2:42][CH2:41][CH2:40]4)[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>[CH:39]1([NH:38][N:29]2[C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:36]([OH:37])=[C:27]([C:22]3[NH:21][C:20]4[CH:44]=[CH:45][C:17]([NH:16][S:2](=[O:4])(=[O:3])[NH:5][C:6]([O:15][CH2:8][C:9]5[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=5)=[O:7])=[CH:18][C:19]=4[S:24](=[O:26])(=[O:25])[N:23]=3)[C:28]2=[O:43])[CH2:40][CH2:41][CH2:42]1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 136358521HCID 136358521, compound

Product 1

HCID 136347220HCID 136347220, compoundYield 662.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of chlorosulfonyl isocyanate (0.051 g, 0.36 mmol) in dichloromethane (2 mL) was treated dropwise with benzyl alcohol (0.039 g, 0.36 mmol) at 0° C., stirred at 25° C. for 30 minutes and treated with a solution of the product of Example 464B (0.127 g, 0.03 mmol) and triethylamine (0.12 g, 1.2 mmol) in dichloromethane (4 mL). The reaction mixture was stirred for 2 hours at 25° C. and partitioned between dichloromethane (10 mL) and 1N aqueous hydrochloric acid (10 mL). The resulting organic layer was separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with 3% methanol in dichloromethane to provide the title compound (0.127 g, 66% yield). 1H NMR (300 MHz, DMSO-d6) δ 1.57 (m, 1 H) 1.70 (m, 1 H) 2.04 (m, 4 H) 3.78 (m, 1 H) 5.12 (s, 2 H) 6.57 (s, 1 H) 7.30 (m, 5 H) 7.44 (t, J=7.54 Hz, 1 H) 7.50 (m, 1 H) 7.66 (m, 2 H) 7.89 (t, J=7.91 Hz, 1 H) 8.07 (d, J=8.09 Hz, 1 H) 8.17 (d, J=8.46 Hz, 1 H) 11.13 (s, 1 H) 12.16 (s, 1 H) 14.15 (s, 1 H) 15.06 (s, 1 H). MS (ESI−) m/z 637 (M−H)−.

Workup

  1. stirringThe reaction mixture was stirred for 2 hours at 25° C.
  2. custompartitioned between dichloromethane (10 mL) and 1N aqueous hydrochloric acid (10 mL)
  3. customThe resulting organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica gel eluting with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-40facb024d1d4922831cfd42ea267936
Source dataset
uspto-grants-2011_03
Patent number
US07902203B2

Reaction notes

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