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Ethanamine, 2,2,2-trifluoro- → (S)-tert-Butyl 1-oxo-1-(2-(2,2,2-trifluoroethylcarbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

HRID 525037
Notes
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Reaction equation

HRID 525037 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][NH2:4].[C:7]([O:11][C:12]([NH:14][C@@H:15]([CH3:28])[C:16]([NH:18][N:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](OC)=[O:25])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8].C[Al](C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[O:17]=[C:16]([NH:18][N:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:24](=[O:25])[NH:4][CH2:3][C:2]([F:6])([F:5])[F:1])[C@@H:15]([NH:14][C:12](=[O:13])[O:11][C:7]([CH3:10])([CH3:9])[CH3:8])[CH3:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 13355Disodium 2,3-dihydroxybutanedioateHCID 16682925TrimethylaluminumHCID 86722033(S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate

Product 1

HCID 86722056(S)-tert-Butyl 1-oxo-1-(2-(2,2,2-trifluoroethylcarbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

2,2,2-Trifluoroethanamine (680 microl, 8.66 mmols) was added to a solution of (S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate (900 mg, 2.89 mmols) in toluene (36 ml). A 2M solution of trimethyl aluminium in toluene (7 ml, 14.00 mmols) was added and it was stirred at 80° C. overnight. Water (50 ml) and a 0.5M solution of sodium tartrate (25 ml) were added. It was extracted with ethylacetate. The combined organic layers were washed with water and brine. It was dried, filtered and concentrated in vacuum. The title compound was obtained (1.021 g, 93%).

Workup

  1. extractionIt was extracted with ethylacetate
  2. washThe combined organic layers were washed with water and brine
  3. customIt was dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-d4d0282b25874c5bb4f22d150445dae7
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09340547B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes