Disodium 2,3-dihydroxybutanedioate → (S)-tert-Butyl 1-oxo-1-(2-(tetrahydro-2H-pyran-4-yl carbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

HRID 525036

Reaction equation

[O:1]1[CH2:6][CH2:5][CH:4]([NH2:7])[CH2:3][CH2:2]1.[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH3:29])[C:17]([NH:19][N:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](OC)=[O:26])=[O:18])=[O:14])([CH3:11])([CH3:10])[CH3:9].C[Al](C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[O:18]=[C:17]([NH:19][N:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25](=[O:26])[NH:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[C@@H:16]([NH:15][C:13](=[O:14])[O:12][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:29]

Participants

Conditions

Temperature: 80 °C

Procedure

Tetrahydro-2H-pyran-4-amine (900 microl, 8.69 mmols) was added to a solution of (S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate (900 mg, 2.89 mmols, preparation 109) 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 (617 mg, 56%).

Workup

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-04de8d8e819c4455b3734c36e5918338
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340547B2

Linked notes

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