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Acrylamide → (2S)-N2-[(3S)-1-(aminocarbonylethyl)pyrrolidin-3-yl]-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide

HRID 412642
Notes
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Reaction equation

HRID 412642 reaction equation
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[C:21]([NH:23][C@H:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)=[O:22]>C(OCC)C.O>[NH3:5].[NH2:5][C:1]([CH2:2][CH2:3][N:26]1[CH2:27][CH2:28][C@H:24]([NH:23][C:21]([C@@H:16]2[CH2:17][CH2:18][CH2:19][CH2:20][N:15]2[C:7]2[O:6][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=2)=[O:22])[CH2:25]1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 6579AcrylamideHCID 57068119(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-pyrrolidin-3-yl]-2-piperidinecarboxamide

Product 2

HCID 222AmmoniaHCID 57170845(2S)-N2-[(3S)-1-(aminocarbonylethyl)pyrrolidin-3-yl]-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamideYield 83.9%

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 3283Diethyl EtherSolvent

Procedure

Acrylamide (11.6 mg) was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-pyrrolidin-3-yl]-2-piperidinecarboxamide (51.6 mg) [see Example 4] in diethyl ether (3 ml). The reaction mixture was refluxed for 18 hours, after which time the ethereal layer was diluted with water. The aqueous layer was separated and then extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 93:7:1, changing to 90:10:1, dichloromethane:methanol:0.88 aqueous ammonia solution to afford (2S)-N2-[(3S)-1-(aminocarbonylethyl)pyrrolidin-3-yl]-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide (26.4 mg) as an off-white foam.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 93:7:1

Sources & evidence

ORD record
ord-de57429a710849f19f7ee529482f6266
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06562964B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes