Benzyl Alcohol → HCID 53639196, compound

HRID 1934696Notes

Reaction equation

HRID 1934696 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[S:10]([N:13]=[C:14]=[O:15])(=[O:12])=[O:11].[C:16]([C:18]1[CH:19]=[CH:20][C:21]([NH:38][C@@H:39]2[CH2:43][CH2:42][NH:41][CH2:40]2)=[C:22]([CH:37]=1)[C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=1)=[O:24])#[N:17].C(N(CC)CC)C>ClCCCl>[CH2:1]([O:8][C:14]([NH:13][S:10]([N:41]1[CH2:42][CH2:43][C@@H:39]([NH:38][C:21]2[CH:20]=[CH:19][C:18]([C:16]#[N:17])=[CH:37][C:22]=2[C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=2)=[O:24])[CH2:40]1)(=[O:12])=[O:11])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 54010737HCID 54010737, compound

Product 1

HCID 53639196HCID 53639196, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent3×

Conditions

Temperature
4 °C

Procedure

A solution of benzyl alcohol (28 mg) in 1,2-dichloroethane (1 mL) was added dropwise to a solution of chlorosulfonyl isocyanate (37 mg) in 1,2-dichloroethane (2 mL) under 5° C. on an ice-salt bath. The mixture was stirred for one and a half hours at 4° C. To the mixture was added dropwise a mixture of (R)-5-cyano-N-(3,4-dimethoxybenzyl)-2-(3-pyrrolidinylamino)benzamide (100 mg) and triethylamine (40 mg) in 1,2-dichloroethane (3 mL) under 5° C. After addition, the reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by a thin layer chromatography developed with 5% methanol in chloroform. The obtained product was triturated with diethyl ether to give (R)-2-[1-(N-benzyloxycarbonylsulfamoyl)pyrrolidin-3-ylamino]-5-cyano-N-(3,4-dimethoxybenzyl)benzamide (65 mg) as a syrup.

Workup

  1. additionTo the mixture was added dropwise
  2. additionAfter addition
  3. temperatureto warm to ambient temperature
  4. stirringstirred overnight
  5. washThe reaction mixture was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by a thin layer chromatography
  9. customThe obtained product was triturated with diethyl ether

Sources & evidence

ORD record
ord-1a92d605c8904749a0c531ba8c2b1036
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

Loading…