Triethylamine → tert-butyl 3-methyl-N-(methylsulfonyl)-L-valinate

HRID 1174376Notes

Reaction equation

HRID 1174376 reaction equation
[CH3:1][C:2]([CH3:13])([CH3:12])[C@@H:3]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[NH2:4].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][C:2]([CH3:13])([CH3:12])[C@@H:3]([C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6])[NH:4][S:22]([CH3:21])(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11252445L-(+)-Ttert-butyl tert-leuc-inate

Product 1

HCID 86599586tert-butyl 3-methyl-N-(methylsulfonyl)-L-valinateYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of tert-butyl 3-methyl-L-valinate (50 mg, 0.223 mmol) in dichloromethane (1 mL) at 0° C. was treated with 4-(dimethylamino)pyridine (5.4 mg, 0.045 mmol), triethylamine (93.4 μL, 0.67 mmol), and methanesulfonyl chloride (34.5 L, 0.45 mmol), and the mixture was warmed to 25° C. for 1 h. The mixture was washed with 5% potassium bisulfate, saturated sodium bicarbonate, brine, and dried over MgSO4, filtered, and the solvents were evaporated to give the crude title compound (59 mg, 100%).

Workup

  1. washThe mixture was washed with 5% potassium bisulfate, saturated sodium bicarbonate, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were evaporated

Sources & evidence

ORD record
ord-36a2dcb7615d4057b1f4c40e17389e13
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

Loading…