Hydrochloric Acid → HCID 131723473, compound

HRID 1278570Notes

Reaction equation

HRID 1278570 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:25])=[C:5]([C:21]([O:23][CH3:24])=[O:22])[CH:6]([C@H:12]2[CH2:16][CH2:15][C@@H:14]([C:17]([O:19]C)=[O:18])[CH2:13]2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[NH:3][C:4]([CH3:25])=[C:5]([C:21]([O:23][CH3:24])=[O:22])[CH:6]([C@H:12]2[CH2:16][CH2:15][C@@H:14]([C:17]([OH:19])=[O:18])[CH2:13]2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131723474HCID 131723474, compound

Product 1

HCID 131723473HCID 131723473, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the compound of Example 2 91.9 mmol) and 4 mL of 2N NaOH in 4 mL methanol was stirred for 2 hours at room temperature. The clear reaction mixture was neutralized by adding 1 N HCl to produce 1,4-dihydro-2,6-dimethyl-4-[cis-3-(hydroxycarbonyl)cyclopentyl]-3,5-pyridine dicarboxylic acid, dimethyl ester. This compound was obtained as a pale crystalline solid: mp 177-179° C.; 1H NMR (DMSO-d6) δ 11.87 (br. s, 1 H), 8.81 (s, 1 H), 3.85 (d, 1 H, J=6.38 Hz), 3.59 (s, 6 H), 2.5 (m, 1 H), 2.22(s, 6 H), 1.6 (m, 4 H), 1.4 (m, 1 H), 1.2 (m, 2 H); 13C NMR (DMSO-d6) δ 177.2, 168.0, 146.3, 99.5, 50.5, 48.1, 41.9, 34.9, 32.2, 27.3, 27.0, 18.1. Analysis calculated for C17H23NO6. 0.67 H2O: C, 58.44; H, 7.02; N, 4.01. Found: C, 58.44; H, 7.10; N, 3.90. A minor trans-isomer was detected but was not isolated.

Sources & evidence

ORD record
ord-37d77b1505244922a0bc601ad24dde08
Source dataset
uspto-grants-2002_09
Patent number
US06444675B2

Reaction notes

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