2-Methylbutylamine → HCID 57274176, compound

HRID 2380120Notes

Reaction equation

HRID 2380120 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C@H:14]1[O:18][C:17](=[O:19])[C@H:16]([C:20]([OH:23])([CH3:22])[CH3:21])[CH2:15]1)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][CH:25]([CH2:28][CH3:29])[CH2:26][NH2:27]>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][CH:11]([CH3:13])[CH3:12])[C@@H:14]([OH:18])[CH2:15][C@@H:16]([C:20]([OH:23])([CH3:22])[CH3:21])[C:17]([NH:27][CH2:26][CH:25]([CH3:24])[CH2:28][CH3:29])=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 72832-MethylbutylamineHCID 14483174HCID 14483174, compound

Product 1

HCID 57274176HCID 57274176, compoundYield 85.3%

Conditions

Temperature
100 °C

Procedure

Following a procedure similar to that described in Preparation 7, 250 mg (0.76 mmoles) of (3S, 5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-3-methylbutyl]-3-(1-hydroxy-1-methylethyl)dihydrofuran-2(3H)-one (prepared as described in Preparation 9) were dissolved in 500 mg (5.75 mmoles) of 2(RS)-methylbutylamine, and the solution was stirred at 100° C. for 3 hours. 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). to give 270 mg (yield 85%) of the title compound as an amorphous substance.

Workup

  1. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  2. customthe residue was purified by medium pressure silica gel column chromatography (
  3. additionby volume mixture of methylene chloride and methanol as eluent)

Sources & evidence

ORD record
ord-0602ceb7021a4be2a07326c430ce7870
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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