Methylamine → HCID 14989084, compound

HRID 2380133Notes

Reaction equation

HRID 2380133 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C@H:17]1[O:21][C:20](=[O:22])[C@H:19]([C:23]([CH2:27][CH3:28])([OH:26])[CH2:24][CH3:25])[CH2:18]1)[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29][NH2:30]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C@@H:17]([OH:21])[CH2:18][C@@H:19]([C:23]([CH2:27][CH3:28])([OH:26])[CH2:24][CH3:25])[C:20]([NH:30][CH3:29])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 14989074HCID 14989074, compound

Product 1

HCID 14989084HCID 14989084, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 361 mg (0.91 mmoles) of (3S, 5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]-3-(1-ethyl-1-hydroxypropyl)dihydrofuran-2(3H)-one (prepared as described in Preparation 21) in 10 ml of methanol was saturated with gaseous methylamine by passing the gas through the solution whilst ice-cooling, and then the flask containing the reaction mixture was stoppered tightly and allowed to stand at room temperature overnight. The reaction mixture was then concentrated by evaporation under reduced pressure, and the residue was purified by medium pressure silica gel column chromatography (using a 20:1 by volume mixture of methylene chloride and methanol as eluent), followed by recrystallization from hexane, to give 372 mg (yield 96%) of the title compound as white crystals, melting at 152°-155° C.

Workup

  1. temperaturecooling
  2. additionthe flask containing the reaction mixture
  3. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  4. customthe residue was purified by medium pressure silica gel column chromatography (
  5. additionby volume mixture of methylene chloride and methanol as eluent),
  6. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-424196fd2b8542daa27260a8555fb58d
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

Loading…