Triethylamine → HCID 58990158, compound

HRID 2261904Notes

Reaction equation

HRID 2261904 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@@:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:11])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.S(=O)(=O)=O.N1C=CC=CC=1>C(Cl)Cl.CS(C)=O.CCOC(C)=O>[CH2:12]([C@:8]([NH:7][C:6](=[O:19])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:11])[CH:9]=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 69790321HCID 69790321, compound

Product 1

HCID 58990158HCID 58990158, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl((1R)-1-benzyl-2-hydroxy-1-methylethyl)carbamate (6.7 g, 25.2 mmol) in DCM (100 mL) and DMSO (25 mL) was added triethylamine (10.5 mL, 75.7 mmol) and sulfurtrioxide-pyridine (10 g, 63.1 mmol). The reaction mixture was stirred at rt for 3.5 h, diluted with EtOAc, washed with 10% KHSO4, saturated NaHCO3, water, brine and aq LiCl, dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography (silica, 0-20% EtOAc/hexanes) to provide tert-butyl ((1R)-1-benzyl-1-methyl-2-oxoethyl)carbamate as a white solid. 1H NMR (400 MHz, CDCl3) δ 9.53 (s, 1H), 7.35-7.22 (m, 3H), 7.12-7.00 (m, 2H), 4.84 (br s, 1H), 3.17 (A of AB, d, J=13.6 Hz, 1H), 3.08 (B of AB, d, J=13.6 Hz, 1H), 1.51 (s, 9H), 1.27 (s, 3H).

Workup

  1. washwashed with 10% KHSO4, saturated NaHCO3, water, brine and aq LiCl
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography (silica, 0-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b341defded1348f8ab53d71b6dc280d6
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

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