Methylamine → (2R, 4S, 5S)-5-{N-[2(R)-Benzyl-3-(morpholinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-2,N-dimethylhexanamide

HRID 1768845Notes

Reaction equation

HRID 1768845 reaction equation
[CH2:1]([C@H:8]([CH2:37][C:38]([N:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1)=[O:39])[C:9]([NH:11][C@H:12]([C:19]([NH:21][C@H:22]([C@H:30]1[O:34][C:33](=[O:35])[C@H:32]([CH3:36])[CH2:31]1)[CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:20])[CH2:13][C:14]1[N:15]=[CH:16][S:17][CH:18]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:46][NH2:47]>CO>[CH2:1]([C@H:8]([CH2:37][C:38]([N:40]1[CH2:41][CH2:42][O:43][CH2:44][CH2:45]1)=[O:39])[C:9]([NH:11][C@H:12]([C:19]([NH:21][C@@H:22]([CH2:23][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1)[C@@H:30]([OH:34])[CH2:31][C@@H:32]([CH3:36])[C:33]([NH:47][CH3:46])=[O:35])=[O:20])[CH2:13][C:14]1[N:15]=[CH:16][S:17][CH:18]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86748372(3R, 5S)-5-[(1S)-1-{N-[2(R)-Benzyl-3-(morpholinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H)-one

Product 1

HCID 15045748(2R, 4S, 5S)-5-{N-[2(R)-Benzyl-3-(morpholinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-6-cyclohexyl-4-hydroxy-2,N-dimethylhexanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 200 mg (0.313 mmole) of (3R, 5S)-5-[(1S)-1{N-[2(R)-benzyl-3-(morpholinocarbonyl)propionyl]-3-(4-thiazolyl)-L-alanyl}amino-2-cyclohexylethyl]-3-methyldihydrofuran-2(3H) -one [prepared as described in Preparation 21(a) above] in 2 ml of methanol was added, whilst ice-cooling, to 2.5 ml of a 40% by volume methanolic solution of methylamine, and the mixture was allowed to stand at room temperature for 1 hour. At the end of this time, any excess of the methylamine and the methanol were removed by distillation under reduced pressure. The resulting residue was dissolved in 4 ml of ethyl acetate, and the solution was allowed to stand overnight at room temperature to deposit crystals. These were collected by filtration to afford 150 mg of the title compound as white crystals, melting at 130°-132° C.

Workup

  1. customAt the end of this time, any excess of the methylamine and the methanol were removed by distillation under reduced pressure
  2. dissolutionThe resulting residue was dissolved in 4 ml of ethyl acetate
  3. waitto stand overnight at room temperature
  4. filtrationThese were collected by filtration

Sources & evidence

ORD record
ord-26e6974768404754852a057a1cc693ad
Source dataset
uspto-grants-1995_01
Patent number
US05378689

Reaction notes

Loading…