Sodium amide → 150610-65-4

HRID 1250321Notes

Reaction equation

HRID 1250321 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[CH:5]([C:19]1[CH:24]=[CH:23][C:22]([O:25][C@H:26]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27]2)=[CH:21][CH:20]=1)[CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([C:17]#[N:18])=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2].[NH2-].[Na+]>C(O)C>[CH2:1]([O:3][C:4](=[O:38])[C@H:5]([C:19]1[CH:24]=[CH:23][C:22]([O:25][C@H:26]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27]2)=[CH:21][CH:20]=1)[CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][C:11]([C:17]#[N:18])=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24533Sodium amide2×HCID 10436518HCID 10436518, compound

Product 1

HCID 9983982150610-65-4Yield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[4-[[(3S)-1-(tert-butoxycarbonyl)-3-pyrrolidinyl]oxy]phenyl]-3-(7-cyano-2-naphthyl)propionic acid ethyl ester (1.90 g, 3.7 mmol) was heated and dissolved in ethanol (6 ml), and the resultant solution was cooled to room temperature with stirring to settle crystals. Subsequently, sodium amide (22 mg, 0.6 mmol) was added thereto, followed by stirring at the same temperature for 30 minutes, then sodium amide (22 mg, 0.6 mmol) was further added, followed by stirring for 18 hours. The crystals were collected through filtration to obtain 1.48 g of the title compound (78% yield). The diastereomer purity of the crystals was 92.3%.

Workup

  1. stirringby stirring at the same temperature for 30 minutes
  2. stirringby stirring for 18 hours
  3. filtrationThe crystals were collected through filtration

Sources & evidence

ORD record
ord-eabb74889e444ad3a447e8672d17b5bb
Source dataset
uspto-grants-2002_01
Patent number
US06337405B1

Reaction notes

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