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Hydrochloric Acid → tert-Butyl (2S)-1-oxo-1-(2-(tetrahydro-2H-pyran-3-ylcarbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

HRID 525039
Notes
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Reaction equation

HRID 525039 reaction equation
C(N(CC)CC)C.[O:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH2:14])[CH2:9]1.Cl.[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH3:37])[C:25]([NH:27][N:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](OC)=[O:34])=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C[Al](C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[O:26]=[C:25]([NH:27][N:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](=[O:34])[NH:14][CH:10]1[CH2:11][CH2:12][CH2:13][O:8][CH2:9]1)[C@@H:24]([NH:23][C:21](=[O:22])[O:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:37]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13355Disodium 2,3-dihydroxybutanedioateHCID 5200320Oxan-3-amineHCID 16682925TrimethylaluminumHCID 86722033(S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate

Product 1

HCID 86722058
tert-Butyl (2S)-1-oxo-1-(2-(tetrahydro-2H-pyran-3-ylcarbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent3×

Conditions

Temperature
80 °C

Procedure

Anhydrous triethylamine (600 μl, 4.31 mmols) was added to a solution of tetrahydro-2H-pyran-3-amine.HCl (600 mg, 4.36 mmols) in toluene (10 ml) and it was stirred at room temperature for 30 min. A solution of (S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate (900 mg, 2.90 mmols) in toluene (36 ml) and a 2M solution of trimethylaluminium in toluene (7 ml, 14 mmols) were added. The solution obtained was stirred at 80° C. for 2 h. Water (70 ml) and a 0.5M sodium tartrate solution (35 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 (750 mg, 68%).

Workup

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

Sources & evidence

ORD record
ord-4f3c9e4f3b6c45da880bdcf15a7164fb
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