N-Methyl-D-glucamine → HCID 25168154, compound

HRID 599486Notes

Reaction equation

HRID 599486 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([S:16][CH:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]3[N:30]([CH3:31])[C:29]([C:32]([OH:34])=[O:33])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH2:19][CH2:18]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[CH3:35][NH:36][CH2:37][C@@H:38]([C@H:40]([C@@H:42]([C@@H:44]([CH2:46][OH:47])[OH:45])[OH:43])[OH:41])[OH:39]>C1COCC1.O.C1COCC1>[NH:36]([CH2:37][C@@H:38]([C@H:40]([C@@H:42]([C@@H:44]([CH2:46][OH:47])[OH:45])[OH:43])[OH:41])[OH:39])[CH3:35].[C:1]([C:5]1[CH:6]=[C:7]([S:16][CH:17]2[CH2:22][CH2:21][N:20]([S:23]([C:26]3[N:30]([CH3:31])[C:29]([C:32]([OH:34])=[O:33])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH2:19][CH2:18]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 8567N-Methyl-D-glucamineHCID 25167880HCID 25167880, compound

Product 1

HCID 25168154HCID 25168154, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 5-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid (Ex. 4, 0.60 g, 1.18 mmol) in THF (2.0 mL) was added a solution of N-methyl-D-glucamine (meglumine, 0.23 g, 1.18 mmol) in water:THF (1:1, 2.0 mL). The resulting solution was stirred at room temperature for 30 min, then concentrated under reduced pressure and the solid residue was triturated with THF (2.0 mL×2). The material was then taken up in Ethyl acetate/hexanes and the resulting slurry was stirred at room temperature overnight. The solid was collected on filter paper and dried in vacuo to afford 0.68 g (82%) of the title compound as a white solid, mp 179-182° C. 1H-NMR (400 MHz, DMSO-d6): δ 7.27 (s, 1H), 7.10 (s, 2H), 6.57 (s, 1H), 5.73 (brs, 2H), 4.66 (brs, 3H), 3.88 (s, 3H), 3.83-3.85 (m, 2H), 3.66-3.67 (m, 2H), 3.57-3.61 (m, 2H), 3.47-3.49 (m, 1H), 3.40-3.44 (m, 1H), 2.92-2.98 (m, 3H), 2.82-2.87 (m, 1H), 2.47 (s, 3H), 2.33-2.38 (m, 2H), 1.90-1.93 (m, 2H), 1.43-1.50 (m, 2H), 1.35 (s, 18H). HRMS (ESI) Calcd. for C32H53N3O10S2, 704.3250 ([M+H]+). Found: 704.3269. Anal. Calcd. for C32H53N3O10S2. 1/2H2O: C, 54.60; H, 7.59; N, 5.97; S, 9.11. Found: C, 54.29; H, 7.45; N, 5.97; S, 8.85.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe solid residue was triturated with THF (2.0 mL×2)
  3. stirringthe resulting slurry was stirred at room temperature overnight
  4. customThe solid was collected
  5. filtrationon filter paper
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4e8980a83f094451b762672771499af1
Source dataset
uspto-grants-2011_03
Patent number
US07897776B2

Reaction notes

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