Methylamine → HCID 14989085, compound

HRID 2380134Notes

Reaction equation

HRID 2380134 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]2([OH:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[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].[CH3:30][NH2:31]>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]1([OH:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[C:20]([NH:31][CH3:30])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 14989075HCID 14989075, compound

Product 1

HCID 14989085HCID 14989085, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 274 mg (0.67 mmoles) of (3S, 5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]-3-(1-hydroxycyclohexyl)dihydrofuran-2(3H)-one (prepared as described in Preparation 22) 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 286 mg (yield 97%) of the title compound as white crystals, melting at 175°-177° 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-95a4be536add4696a13bc8f0d44498e2
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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