Diisopropylethylamine → N-Acetyl-D-Galactosamine

HRID 1471309노트

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HRID 1471309 반응식
C([O:4][C@H:5]1[C@@H:10]([O:11]C(=O)C)[C@@H:9]([CH2:15][O:16]C(=O)C)[O:8][C@@H:7]([O:20]CCOCCOCCOCC(O)=O)[C@@H:6]1[NH:34][C:35](=[O:37])[CH3:36])(=O)C.Cl.C(OC(=O)[C@@H](NC(=O)[C@@H](N)CCCCN)CCCCN)C1C=CC=CC=1.CCN(C(C)C)C(C)C.ON1C2N=CC=CC=2N=N1>C(Cl)Cl.CN(C=O)C>[OH:20][CH:7]1[O:8][C@H:9]([CH2:15][OH:16])[C@H:10]([OH:11])[C@H:5]([OH:4])[C@H:6]1[NH:34][C:35]([CH3:36])=[O:37]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 58409186(2-{2-[2-((2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acidHCID 67350397(S)-6-amino-2-((5)-2,6-diamino-hexanoylamino)-hexanoic acid benzyl ester hydrochloride

생성물 1

HCID 35717N-Acetyl-D-Galactosamine수율 142.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

The above prepared (2-{2-[2-((2R,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid (2.820 g, 5.246 mmol) and (S)-6-amino-2-((S)-2,6-diamino-hexanoylamino)-hexanoic acid benzyl ester hydrochloride (preparation see below, 0.829 g, 1.749 mmol) were dissolved in a mixture of 32 mL of CH2Cl2 and 3.2 mL of DMF, treated successively with Hünig's base (2.096 ml, 12.25 mmol), 1-hydroxy-7-azabenzotriazole (0.714 g, 5.248 mmol) and 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride (1.006 g, 5.248 mmol), and stirred over night at ambient temperature. All volatiles were removed i.V., and the crude reaction mixture purified by preparative HPLC (38 runs, Gemini, 5μ, C18) to give after lyophilization 1.650 g of the title product as white powder. MS (ISP): 1945.8 [M+Na]+. NMR (600 MHz, DMSO).

후처리

  1. customAll volatiles were removed i.V
  2. custom, and the crude reaction mixture
  3. custompurified by preparative HPLC (38 runs, Gemini, 5μ

출처 및 근거

ORD 기록
ord-dd8cda5d5e8f4e428df26365dd9cce52
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09011919B2

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