Dicyclohexylcarbodiimide → 2-N-(4-Methoxy-2,3,6-trimethyl-benzenesulfonyl)-4-N-(beta-D-galactopyranosyl)-L-asparaginyl-4-amidino-D-phenylalanine-piperidide hydrochloride

HRID 743674

반응식

HRID 743674 반응식
[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([S:11]([NH:14][C@H:15]([C:20]([NH:22][C@@H:23]([C:34]([N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[O:35])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31](=[NH:33])[NH2:32])=[CH:27][CH:26]=2)=[O:21])[CH2:16][C:17](=[O:19])[NH2:18])(=[O:13])=[O:12])=[C:6]([CH3:42])[C:5]=1[CH3:43].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[C@@H:69]1(N)[O:77][C@H:76]([CH2:78][OH:79])[C@H:74]([OH:75])[C@H:72]([OH:73])[C@H:70]1[OH:71]>CN(C=O)C.ClCCl>[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH3:10])[C:7]([S:11]([NH:14][C@H:15]([C:20]([NH:22][C@@H:23]([C:34]([N:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)=[O:35])[CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:31](=[NH:32])[NH2:33])=[CH:29][CH:30]=2)=[O:21])[CH2:16][C:17](=[O:19])[NH:18][C@@H:69]2[O:77][C@H:76]([CH2:78][OH:79])[C@H:74]([OH:75])[C@H:72]([OH:73])[C@H:70]2[OH:71])(=[O:13])=[O:12])=[C:6]([CH3:42])[C:5]=1[CH3:43]

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 11095207(2R,3R,4S,5R,6R)-2-Amino-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolHCID 228655222-N-(4-Methoxy-2,3,6-trimethyl-benzenesulfonyl)-L-asparaginyl-4-amidino-D-phenylalanine-piperidide hydrochloride

생성물 1

HCID 867498292-N-(4-Methoxy-2,3,6-trimethyl-benzenesulfonyl)-4-N-(beta-D-galactopyranosyl)-L-asparaginyl-4-amidino-D-phenylalanine-piperidide hydrochloride

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

2-N-(4-Methoxy-2,3,6-trimethyl-benzenesulfonyl)-L-asparaginyl-4-amidino-D-phenylalanine-piperidide hydrochloride (1.0 g), HOBt (0.23 g) and DCCI (0.37 g) were dissolved in DMF and dichloromethane 1:1 (50 mL) and, after 0.5 h of stirring, β-D-galactopyranosyl-amine (1.0 g) was added. The reaction mixture was stirred for 48 h at room temperature and then filtered and concentrated by evaporation in vacuo. The residue was dissolved in ethyl acetate and washed with water. The crude product was purified by column chromatography on silica gel with chloroform/methanol 5:1. Yield: 1.2 g. TLC analysis: Rf=0.73 (chloroform/methanol 3:1). Barium oxide (0.25 g) was added to a solution of the intermediate compound (1.2 g) in chloroform/methanol 2:1 (100 mL), and the mixture was stirred for 2 h and then filtered. The flitrate was neutralized with methanolic HCl and concentrated by evaporation in vacuo. The residue was purified by column chromatography (Sephadex LH 20). Yield: 1.0 g. TLC analysis: Rf=0.042 (chloroform/methanol 3:1). [α]D +19.3° (c=1 in methanol). M.p. 186°-190° C.

후처리

  1. filtrationfiltered
  2. concentrationconcentrated by evaporation in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. customThe crude product was purified by column chromatography on silica gel with chloroform/methanol 5:1
  6. additionBarium oxide (0.25 g) was added to a solution of the intermediate compound (1.2 g) in chloroform/methanol 2:1 (100 mL)
  7. stirringthe mixture was stirred for 2 h
  8. filtrationfiltered
  9. concentrationconcentrated by evaporation in vacuo
  10. customThe residue was purified by column chromatography (Sephadex LH 20)

출처 및 근거

ORD 기록
ord-13a90241968442bca6897c65371ce9a1
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05556941

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