N-Methyl-D-glucamine → 3-[(2-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carbonyl)-amino]-benzoic acid

HRID 1018303Notes

Reaction equation

HRID 1018303 reaction equation
[C:1]12([CH2:11][C:12]3[NH:13][C:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][C:16]=3[C:17](O)=[O:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C([O:33][C:34](=[O:42])[C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([NH2:41])[CH:36]=1)C1C=CC=CC=1.CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.O.O1CCOCC1>O>[C:1]12([CH2:11][C:12]3[NH:13][C:14]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:15][C:16]=3[C:17]([NH:41][C:37]3[CH:36]=[C:35]([CH:40]=[CH:39][CH:38]=3)[C:34]([OH:33])=[O:42])=[O:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 8567N-Methyl-D-glucamineHCID 113820842-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carboxylic acidHCID 15428374Benzyl 3-aminobenzoateHCID 218864351,4-Dioxane--water (1/1)

Product 1

HCID 98901983-[(2-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carbonyl)-amino]-benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The benzyl ester of the title compound was prepared by reacting 2-adamantan-1-ylmethyl-5-phenyl-1H-pyrrole-3-carboxylic acid (Example 1, step c) with 3-amino-benzoic acid benzyl ester according to the procedure of Example 1, step d. This was converted to the title compound using the procedure of Example 1, step e. 1H NMR (300 MHz, d6-DMSO) 11.19 (1H, s), 9.62 (1H, s), 8.37 (1H, s), 7.97 (1H, d) 7.66 (2H, d), 7.58 (1H, d), 7.39 (3H, m), 7.16 (2H, m), 2.84 (2H, s), 1.88 (3H, br s), 1.54 (12H, m). The product was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 62.82; H, 7.38; N, 5.82%; C36H47N3O8.2.0 H2O requires: C, 63.04; H, 7.50; N, 6.12%.

Sources & evidence

ORD record
ord-02b53532c81e4d589a5a3aecb5cfe9e8
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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