SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 11, 2008, Pages 1651-1656

A novel solid-phase synthetic method for 1,4-benzodiazepine-2,5-dione derivatives

(4) Jeon, Moon Kook a Kwon, Jeong Jin a Kim, Myung Su a Gong, Young Dae a

a Korea Research Institute of Chemical Technology (South Korea)

Author keywords

Anthranilic acid; Benzodiazepine; Combinatorial chemistry; Cyclative cleavage; Solid phase synthesis

Indexed keywords

1,4 BENZODIAZEPINE 2,5 DIONE DERIVATIVE; AMINO ACID; ANTHRANILIC ACID DERIVATIVE; BENZODIAZEPINE DERIVATIVE; G 7446; G 7570; RESIN; VAD 463;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CROSS COUPLING REACTION; CYCLIZATION; DRUG ISOLATION; DRUG PURITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SOLID PHASE SYNTHESIS;

EID: 48449096719 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078484 Document Type: Article

Times cited : (10)

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77
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- Although several other conditions for the resin 5a and N-Fmoc-protected phenylalanine (R2, Bn, 3 equiv) were examined varying coupling agent [DCC, DIC, EDC, O-benzotriazole-N,N, N′,N′-tetramethyluronium hexafluorophosphate (HBTU, 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, O-(benzotriazol-1-yl)-N,N,N′, N′-tetramethyluronium tetrafluoroborate (TBTU, BOP, PyBOP, 2-chloro-1,3-dimethylimidazolidium hexafluorophosphate (CIP, 1,1′-carbonyldiimidazole (CDI, N,N′-disuccinimidyl carbonate (DSC, or diphenylphosphoryl azide (DPPA, additive [none, N-hydroxybenzotriazole (HOBt, 1-hydroxy-7-azabenzotriazole (HOAt, or N-hydroxysuccinimide (HOSu, base [none, pyridine, Et3N, diisopropylethylamine (DIEA, or NMM, solvent [CH2Cl2, THF, DMF, or N,N-dimethyl-acetamide DMA, at r.t. or elevated te
- 2, THF, DMF, or N,N-dimethyl-acetamide (DMA)] at r.t. or elevated temperatures, they did not bring any significant change on the resin 5a when judged on the basis of on-bead ATR-FTIR spectroscopy.

78
- 70350460403
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81
- 48449095022
- Representative Procedures for Preparation of Compounds 3 Preparation of (S)-2-{Benzyl[2-(Fmoc-amino)-3-phenylpropionyl]amino} benzoate Resin (6a; R4, H, R1, Bn, R2, Bn, To a mixture of the resin 5a2a,b (R4, H, R1, Bn, 100 mg, theoretically 0.077 mmol) and Fmoc-phenylalanine (93 mg, 0.23 mmol) in CH2Cl2 (2 mL) at r.t. were added pyridine (37 mg, 0.46 mmol) and phosphorous oxychloride (37 mg, 0.23 mmol, The mixture was stirred at r.t. for 10 h and the resin was filtered, washed several times with CH 2Cl2, DMF, MeOH, H2O, and MeOH, and dried in a vacuum oven to give 6a (124 mg, On-bead ATR-FTIR: 3418 (NH, 3028, 2921, 1722 (OC=O, NH-Fmoc, overlapped, 1664 (NC=O, 1601, 1512, 1492, 1451, 1241, 1076, 1028, 824, 757, 738, 697 cm-1. Preparation of (S)-1,3-Dibenzyl-1,4-benzodiazepine-2,5-dione 3a; R4, H, R 1
- 4 = 7-BzNH)

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