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

HRID 29182

Reaction equation

HRID 29182 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-methoxybenzenesulfon-amide (0.12 mmol, 50 mg), 1-([(35)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): δ 7.74-7.70 (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-30c21f42147e40b6b8ff8af4fc2409ba
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Linked notes

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