Diisopropylethylamine → N-Acetyl-D-Galactosamine

HRID 1471309Notes

Reaction equation

HRID 1471309 reaction equation
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]

Participants

7

Reactant 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

Product 1

HCID 35717N-Acetyl-D-GalactosamineYield 142.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-dd8cda5d5e8f4e428df26365dd9cce52
Source dataset
uspto-grants-2015_04
Patent number
US09011919B2

Reaction notes

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