Formic Acid → N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)formamide

HRID 2199707Notes

Reaction equation

HRID 2199707 reaction equation
[NH2:1][CH2:2][C@@H:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C:16]3=[O:21])=[CH:11][CH:10]=2)[CH2:4]1.[CH:22](O)=[O:23]>O>[O:8]=[C:6]1[N:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][C:16]3=[O:21])=[CH:11][CH:10]=2)[CH2:4][C@H:3]([CH2:2][NH:1][CH:22]=[O:23])[O:7]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 11346837(S)-4-(4-(5-(aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one

Product 1

HCID 90258317N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)formamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

In a four neck round bottom flask charged with 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl}morpholin-3-one free base (50 g) toluene (350 ml) and formic acid (21.63 g). Reaction mass then heated azeotropically to 110-120° C. employing dean-stark apparatus for 3 to 4 h. (water removed azeotropically) Reaction mass is cooled to 25 to 30° C. Obtained solid is filtered off and washed by toluene.

Workup

  1. customReaction mass
  2. customfor 3 to 4 h.
  3. customremoved azeotropically)
  4. customReaction mass
  5. temperatureis cooled to 25 to 30° C
  6. customObtained solid
  7. filtrationis filtered off
  8. washwashed by toluene

Sources & evidence

ORD record
ord-e959a36f30a84c2184ee2faa6ebb2c8a
Source dataset
uspto-grants-2016_06
Patent number
US09359341B2

Reaction notes

Loading…