N-Methyl-D-glucamine → HCID 18405392, compound

HRID 1018385Notes

Reaction equation

HRID 1018385 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+:6]1C=CC=CC=1.[C:12]12([CH2:20]O)[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[CH2:14][CH2:13]2.[CH:22]1([CH:28]=O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C([O:37][C:38](=[O:47])[C:39]1[CH:44]=[C:43]([NH2:45])[CH:42]=[CH:41][C:40]=1[CH3:46])C1C=CC=CC=1.C(OC(=O)[C:57]1[CH:62]=[CH:61]C=C(N)C=1)C1C=CC=CC=1.C[NH:66][CH2:67][C@@H:68]([C@H]([C@@H]([C@@H](CO)O)O)O)[OH:69].O.[O:79]1[CH2:84][CH2:83]OCC1>>[C:22]12([O:69][CH2:68][C:67]3[NH:66][C:20]([C:12]45[CH2:13][CH2:14][CH:15]([CH2:16][CH2:17]4)[CH2:18][CH2:19]5)=[N:6][C:83]=3[C:84]([NH:45][C:43]3[CH:42]=[CH:41][C:40]([CH3:46])=[C:39]([CH:44]=3)[C:38]([OH:37])=[O:47])=[O:79])[CH2:23][CH:24]3[CH2:25][CH:26]([CH2:61][CH:62]([CH2:57]3)[CH2:28]1)[CH2:27]2

Participants

8

Reactant 7

HCID 8567N-Methyl-D-glucamineHCID 16275CyclohexanecarboxaldehydeHCID 13245694{bicyclo[2.2.2]octan-1-yl}methanolHCID 15428374Benzyl 3-aminobenzoateHCID 218864351,4-Dioxane--water (1/1)HCID 538373385-Amino-2-methyl-benzoic acid benzyl esterHCID 178418287HCID 178418287, compound

Product 1

HCID 18405392HCID 18405392, compound

Procedure

The title compound was prepared according to the procedure of Example 216, with the modification that bicyclo[2.2.2]oct-1-yl-carbaldehyde (prepared by pyridinium chlorochromate oxidation of bicyclo[2.2.2]oct-1-yl-methanol (C. A. Grob, M. Ohta, E. Renk and A. Weiss, Helv. Chim. Acta 1958, 41, 1191)) was used in step d instead of cyclohexanecarboxaldehyde and 5-amino-2-methyl-benzoic acid benzyl ester replaced 3-amino-benzoic acid benzyl ester in step f. 1H NMR (300 MHz, d6-DMSO) 12.05 (1H, br s), 9.48 (1H, br s), 8.22 (1H, br s), 7.76 (1H, dd), 7.21 (1H, d), 4.76 (2H, s), 2.45 (3H, s), 2.08 (3H, br s), 1.88-1.73 (12H, m), 1.62-1.51 (13H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.69; H, 8.29; N, 7.28%; C38H56N4O9.2.0 H2requires: C, 60.94; H, 8.08; N, 7.48%.

Sources & evidence

ORD record
ord-714e54b9bef542a8bcb0cd4e27e44a01
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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