Ethyl (2R,3R)-3-{[(2S)-4-methyl-1-oxo-1-{4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl}pentan-2-yl]carbamoyl}oxirane-2-carboxylate → HCID 23700901, compound

HRID 2164878Notes

Reaction equation

HRID 2164878 reaction equation
[OH-].[Na+:2].C(O)C.[CH3:6][CH:7]([CH3:42])[CH2:8][C@H:9]([NH:31][C:32]([C@@H:34]1[O:36][C@H:35]1[C:37]([O:39]CC)=[O:38])=[O:33])[C:10]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[C:20]=2[O:29][CH3:30])[CH2:14][CH2:13]1)=[O:11]>C(O)C>[CH3:6][CH:7]([CH3:42])[CH2:8][C@H:9]([NH:31][C:32]([C@@H:34]1[O:36][C@H:35]1[C:37]([O-:39])=[O:38])=[O:33])[C:10]([N:12]1[CH2:13][CH2:14][N:15]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[C:20]=2[O:29][CH3:30])[CH2:16][CH2:17]1)=[O:11].[Na+:2]

Participants

4

Reactant 2

HCID 6917749Ethyl (2R,3R)-3-{[(2S)-4-methyl-1-oxo-1-{4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl}pentan-2-yl]carbamoyl}oxirane-2-carboxylateHCID 23692425Sodium hydroxide ethanol

Product 1

HCID 23700901HCID 23700901, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under cooling with ice, a 0.48N sodium hydroxide-ethanol solution (9.48 ml) was added to an ethanol solution (20 ml) of ethyl trans-3-[(s)-3-methyl-1-{4-(2,3,4-trimethoxyphenylmethyl)piperazine-1-yl carbonyl}butylcarbamoyl]oxirane-2-carboxylate (2.38 g) obtained above, and the mixture was stirred at room temperature for 2.5 hours. After removal of ethanol by distillation under reduced pressure, water was added, and any insoluble matters were removed by filtration using sellaite. The filtrate was concentrated and dried under reduced pressure to yield 2.31 g of sodium trans-3-[(s)-3-methyl-1-{4-(2,3,4-trimethoxyphenylmethyl)piperazine-1-yl carbonyl}butylcarbamoyl]oxirane-2-carboxylate as a light yellow powder (yield: 98%).

Workup

  1. temperatureUnder cooling with ice
  2. customobtained above, and the mixture
  3. customAfter removal of ethanol
  4. distillationby distillation under reduced pressure, water
  5. additionwas added
  6. customany insoluble matters were removed by filtration
  7. concentrationThe filtrate was concentrated
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-7322cfa1c394484c86b4ae45641b787e
Source dataset
uspto-grants-1985_03
Patent number
US04507297

Reaction notes

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