Dicyclohexylcarbodiimide → Divinylbenzene-styrene

HRID 1582568

反応式

HRID 1582568 の反応式
C(S(N[C@H](C(OC(C)(C)C)=O)CC(O)=O)(=O)=O)CCCCC[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C>[CH:15]([C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:8]=[CH2:7])=[CH2:16].[CH2:16]=[CH:15][C:14]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 20726730N-hexadecylsulfonyl-(O-t-butyl)-L-aspartic acid

生成物 1

HCID 174664Divinylbenzene-styrene収率 10,803.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

N-Hexadecylsulfonyl-(O-t-butyl)-L-aspartic acid (189 mg, 0.395 mmole), 1-hydroxybenzotriazole (55.1 mg, 0.395 mmole) and dicyclohexylcarbodiimide (82.5 mg, 0.395 mmole) in 0.50 mL DMF was stirred at room temperature for 45 minutes. A 0.050 mL aliquot of this solution was added to the tetrabutylammonium salt of 6 (25 mg) in 0.20 mL of DMF and stirred at room temperature for 60 minutes. The reaction mixture was quenched by dilution with 8 mL of 25% acetonitrile (AcN) 0.12 M in ammonium phosphate (pH 7.2), aged at room temperature, then filtered through a membrane (Whatman GD/X). The product was isolated from the filtrate by low resolution reverse phase chromatography on a 5 g styrene-divinylbenzene resin cartridge (25×45 mm, Supelco EnviChrom-P). The sample-loaded cartridge was eluted with stepwise increasing concentrations of AcN in sodium phosphate (aqueous pH 6.9); product was eluted with 57% AcN 0.010 M in pH 6.9 buffer. Product-containing fractions were pooled, diluted with an equal volume of distilled water and then desalted on the same 5g resin cartridge which had been rinsed with 75% and 25% AcN. The diluted fraction pool was applied to the cartridge, which was rinsed with 16 mL 25% AcN 0.125 M in ammonium phosphate (pH 7.2), then 24 mL salt-free 25% AcN. The product was stripped from the cartridge with 48 mL 67% AcN. AcN was removed under vacuum from the strip fraction and the aqueous solution was freeze dried to give the desired product. Yield: 4.7 mg of a white solid, 69% by HPLC (215 nm area %); C62H104N12O20S; FABMS m/z 1392 (M+Na)+. (calc. for C62H104N12O20S+Na, 1391.7).

後処理

  1. customThe reaction mixture was quenched by dilution with 8 mL of 25% acetonitrile (AcN) 0.12 M in ammonium phosphate (pH 7.2)
  2. customaged at room temperature
  3. filtrationfiltered through a membrane (Whatman GD/X)

出典と根拠

ORDレコード
ord-fb9bcf5941ed4b208344072c9e0de8c2
出典データセット
uspto-grants-2004_05
特許番号
US06737403B2

関連ノート

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