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

HRID 525039Notes

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]

Participants

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

customThe solution obtained
extractionIt was extracted with ethylacetate
washThe combined organic layers were washed with water and brine
customIt was dried
filtrationfiltered
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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