Tetrahydrofuran → (3s)Tetrahydro-3-furanyl n-((1s,2r)-1-benzyl-3-sec-butoxy[(4-methoxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

HRID 1166491Notes

Reaction equation

HRID 1166491 reaction equation
[NH2:1][C@@H:2]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C@H:3]([OH:22])[CH2:4][N:5](OC(CC)C)[S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[O:30]1[CH2:34][CH2:33][C@H:32]([O:35][C:36]([O:38]N2C(=O)CCC2=O)=O)[CH2:31]1.[CH:46](N(C(C)C)CC)(C)C.[CH2:55]1C[O:58][CH2:57][CH2:56]1>>[CH2:23]([C@H:2]([NH:1][C:36](=[O:38])[O:35][C@H:32]1[CH2:33][CH2:34][O:30][CH2:31]1)[C@@H:3]([OH:22])[CH:4]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=[O:7])=[O:8])[O:58][CH:57]([CH2:56][CH3:55])[CH3:46])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 11229944Carbonic Acid 2,5-Dioxopyrrolidin-1-yl (S)-Tetrahydrofuran-3-yl EsterHCID 57264501N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(sec-butoxy)-4-methoxybenzene-sulfonamide

Product 1

HCID 69222762(3s)Tetrahydro-3-furanyl n-((1s,2r)-1-benzyl-3-sec-butoxy[(4-methoxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate

Procedure

N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(sec-butoxy)-4-methoxybenzenesulfonamide (0.12 mmol, 50 mg), 1-([(3S)tetrahydro-3-furanyloxy]carbonyloxy)dihydro-1H-pyrrole-2,5-dione (0.12 mmol, 29 mg), diisopropylethylamine (0.18 mmol, 0.031 mL) and anhydrous THF (1 mL) were combined and stirred at room temperature for 20 hours. The reaction product was concentrated to a residue, purified directly by silica gel chromatography (2:1 hexanes/ethyl acetate) and crystallized from diethyl ether providing 40 mg (63%) of a white crystal. H1-NMR (CDCl3): δ7.74-7.70 (2H,m), 7.30-7.17 (6H,m), 7.00-6.96 (2H,m), 5.11 (1H,bs), 4.75 (1H,bs), 4.31-4.30 (1H,m), 3.87 (3H,s), 3.87-3.75 (6H,m), 3.65-3.60 (1H,m), 3.21-2.64 (1H,bs), 2.89 (2H,bs), 2.15-2.01 (1H,m), 1.95-1.78 (1H,m), 1.78-1.58 (1H,m), 1.47-1.32 (1H,m), 1.24-1.13 (3H,m), 0.94-0.84 (3H,m); MS (ESI): M+Na=560.

Workup

  1. concentrationThe reaction product was concentrated to a residue
  2. custompurified directly by silica gel chromatography (2:1 hexanes/ethyl acetate)
  3. customcrystallized from diethyl ether providing 40 mg (63%) of a white crystal

Sources & evidence

ORD record
ord-e5adf598a5bb4f678d6bd4acd65e4ec7
Source dataset
uspto-grants-2003_09
Patent number
US06613743B2

Reaction notes

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