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

HRID 29182

反応式

HRID 29182 の反応式
[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

参加物

5

反応物 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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-30c21f42147e40b6b8ff8af4fc2409ba
出典データセット
uspto-grants-2008_09
特許番号
US07419967B2

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