Morpholine → HCID 70049647, compound

HRID 1780255Notes

Reaction equation

HRID 1780255 reaction equation
[N+](C1C=CC([O:8][C:9]([N:11]([C:13]2[CH:55]=[CH:54][C:16]([O:17][CH2:18][C:19]([NH:21][C@H:22]([C:27]([NH:29][C@@H:30]([CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C@H:31]([OH:46])[C:32]([N:34]3[CH2:45][CH2:44][CH2:43][C@H:35]3[C:36]([NH:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:33])=[O:28])[CH2:23][C:24](=[O:26])[NH2:25])=[O:20])=[CH:15][CH:14]=2)[CH3:12])=O)=CC=1)([O-])=O.[NH:58]1[CH2:63][CH2:62][O:61][CH2:60][CH2:59]1>>[O:61]1[CH2:62][CH2:63][N:58]([C:9]([N:11]([C:13]2[CH:55]=[CH:54][C:16]([O:17][CH2:18][C:19]([NH:21][C@H:22]([C:27]([NH:29][C@@H:30]([CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C@H:31]([OH:46])[C:32]([N:34]3[CH2:45][CH2:44][CH2:43][C@H:35]3[C:36]([NH:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:33])=[O:28])[CH2:23][C:24](=[O:26])[NH2:25])=[O:20])=[CH:15][CH:14]=2)[CH3:12])=[O:8])[CH2:59][CH2:60]1

Participants

3

Reactant 2

HCID 8083Morpholine2×HCID 70059124HCID 70059124, compound

Product 1

HCID 70049647HCID 70049647, compound

Procedure

A solution of 47 mg (0.060 mmol) of 1-[(2S,3S)-3-{N2 -[4-(P-N-nitrophenoxycarbonyl-N-methylamino)-phenoxy]acetyl-L-asparaginyl}amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide (prepared as described in Example 42) dissolved in 0.5 ml of morpholine was allowed to stand at room temperature for 6 days. At the end of this time, the reaction mixture was freed from an excess of morpholine by distillation under reduced pressure, and the residue was diluted with chloroform and then washed with water. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by preparative thin layer chromatography, using a 8:1 by volume mixture of methylene chloride and methanol as the developing solvent, to give 30 mg of the title compound as a colorless powder, melting at 112°-114° C.

Workup

  1. distillationby distillation under reduced pressure
  2. additionthe residue was diluted with chloroform
  3. washwashed with water
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by preparative thin layer chromatography
  7. additionby volume mixture of methylene chloride and methanol as the developing solvent

Sources & evidence

ORD record
ord-b66a918af4b4424a86a4a5b47ca6b2c4
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

Loading…