Pyridine → {3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-isopropylsulfanyl-phenyl}-carbamic acid phenyl ester

HRID 735527Notes

Reaction equation

HRID 735527 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[C:11]([O:15][C:16](=[O:31])[N:17]([CH2:19][C:20]1[CH:25]=[C:24]([NH2:26])[CH:23]=[CH:22][C:21]=1[S:27][CH:28]([CH3:30])[CH3:29])[CH3:18])([CH3:14])([CH3:13])[CH3:12].N1C=CC=CC=1>C(Cl)Cl.O>[C:5]1([O:4][C:2](=[O:3])[NH:26][C:24]2[CH:23]=[CH:22][C:21]([S:27][CH:28]([CH3:30])[CH3:29])=[C:20]([CH2:19][N:17]([C:16]([O:15][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:31])[CH3:18])[CH:25]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 57842879tert-Butyl-(5-amino-2-(isopropylthio)benzyl)(methyl)carbamate

Product 1

HCID 57842736{3-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-4-isopropylsulfanyl-phenyl}-carbamic acid phenyl esterYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Phenyl chloroformate (0.204 mL, 1.62 mmol) was added dropwise to a solution of 16E (0.48 g, 1.55 mmol) in pyridine (0.193 mL, 2.38 mmol) and DCM (3.5 mL) at 0° C. The reaction mixture was stirred at rt for 1 h. The reaction mixture was diluted with water and extracted with DCM (2×). The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (gradient from 0 to 50% ethyl acetate in hexanes) to give 16F (0.609 g, 91%) as a white foam.

Workup

  1. extractionextracted with DCM (2×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel chromatography (gradient from 0 to 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0e8f16a1eea24d6b85ccc87781d629d8
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…