Dimethyl Sulfoxide → tert-Butyl N-(3-oxopropyl)carbamate

HRID 1481639Notes

Reaction equation

HRID 1481639 reaction equation
CS(C)=O.C(N(CC)CC)C.[C:12]([O:16][C:17]([NH:19][CH2:20][CH2:21][CH2:22][OH:23])=[O:18])([CH3:15])([CH3:14])[CH3:13]>ClCCl>[C:12]([O:16][C:17]([NH:19][CH2:20][CH2:21][CH:22]=[O:23])=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 3838134tert-butyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 10910051tert-Butyl N-(3-oxopropyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dimethyl sulfoxide (321 mL, 4.5 mol) and triethylamine (941 mL, 6.75 mol) were added to a solution of 3-tert-butoxycarbonylamino-1-propanol (262.6 g, 1.5 mol) in dichloromethane (1.2 L) at 0° C. Sulfur trioxide pyridine complex (286.4 g, 1.8 mol) was added in 6 portions. The reaction mixture was then stirred for 30 min at 0° C. and for 30 min at room temperature. The reaction was cooled down to 0° C., quenched with 1N hydrochloric acid, washed with brine (2×500 mL), dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 3-(tert-butoxycarbonylamino)propionaldehyde.

Workup

  1. additionSulfur trioxide pyridine complex (286.4 g, 1.8 mol) was added in 6 portions
  2. temperatureThe reaction was cooled down to 0° C.
  3. customquenched with 1N hydrochloric acid
  4. washwashed with brine (2×500 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7cbae2ac11514b9790144a042a393c87
Source dataset
uspto-grants-2016_08
Patent number
US09409945B2

Reaction notes

Loading…