Morpholine → HCID 86750823, compound

HRID 1780253Notes

Reaction equation

HRID 1780253 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:8][C:9]([N:11]([C:13]1[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]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C@H:31]([OH:46])[C:32]([N:34]2[CH2:45][CH2:44][CH2:43][C@H:35]2[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]=1)[CH3:12])=[O:10]>C(Cl)(Cl)Cl>[C:5]([OH:10])(=[O:4])[CH3:6].[O:4]1[CH2:5][CH2:6][N:1]([CH2:8][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]([CH3:40])([CH3:41])[CH3:42])=[O:37])=[O:33])=[O:28])[CH2:23][C:24](=[O:26])[NH2:25])=[O:20])=[CH:15][CH:14]=2)[CH3:12])=[O:10])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 70049329HCID 70049329, compound

Product 1

HCID 86750823HCID 86750823, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.11 ml (1.3 mmol) of morpholine was added to 100 mg (0.13 mmol) of 1-[(2S,3S)-3-{N2 -[4-(N-bromoacetyl-N-methylamino)phenoxy]acetyl-L-asparaginyl}amino-2-hydroxy-4-phenylbutyryl]-N-t-butyl-L-prolinamide (prepared as described in Example 30), and the resulting mixture was allowed to stand for 4 days. At the end of this time, the reaction mixture was diluted with chloroform, and the diluted solution was washed with water. The solvent was then removed by distillation under reduced pressure, and the residue was purified by preparative thin layer chromatography, using a 16:4:1 by volume mixture of chloroform, methanol and 32% v/v aqueous acetic acid. The product was triturated with diethyl ether, to obtain 49 mg of the title compound as a colorless powder, melting at 114°-122° C.

Workup

  1. washthe diluted solution was washed with water
  2. customThe solvent was then removed by distillation under reduced pressure
  3. customthe residue was purified by preparative thin layer chromatography
  4. additionby volume mixture of chloroform, methanol and 32% v/v aqueous acetic acid
  5. customThe product was triturated with diethyl ether

Sources & evidence

ORD record
ord-4d7f04dca8f342aca5ffa7093d47f52f
Source dataset
uspto-grants-1997_05
Patent number
US05629406

Reaction notes

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