Water → HCID 86705551, compound

HRID 2279566Notes

Reaction equation

HRID 2279566 reaction equation
CS(O[CH2:6][CH2:7][C@@H:8]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=1)(=O)=O.[Na+].[I-:26].O>C1COCC1.CC(C)=O>[Cl:16][C:11]1[CH:10]=[C:9]([C@H:8]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:7][CH2:6][I:26])[CH:14]=[CH:13][C:12]=1[Cl:15]

Participants

6

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 86705550HCID 86705550, compound

Product 1

HCID 86705551HCID 86705551, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 364 (750 mg, 1.88 mmol) in THF (25 mL) and acetone (5 mL) at RT was added NaI (1411 mg, 9.41 mmol) and stirring was continued overnight. The mixture was poured into water, extracted with EtOAc, washed with brine, dried (MgSO4), and concentrated to afford 810 mgs (100%) of (R)-tert-butyl 1-(3,4-dichlorophenyl)-3-iodopropylcarbamate (366).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c1ea5848b9e649ed87045036c80305a3
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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