Hydrochloric Acid → HCID 44253058, compound

HRID 18957Notes

Reaction equation

HRID 18957 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:27])[C@@H:12]([N:19]2[CH2:23][C:22]([O:24][CH3:25])=[CH:21][C:20]2=[O:26])[CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:6][CH:5]=1.O.[OH-].[Li+].Cl>O1CCCC1.O.ClCCl>[CH:14]1([CH2:13][C@H:12]([N:19]2[CH2:23][C:22]([O:24][CH3:25])=[CH:21][C:20]2=[O:26])[C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:28])=[O:2])=[CH:5][N:6]=2)=[O:27])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 44253057HCID 44253057, compound

Product 1

HCID 44253058HCID 44253058, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-[(S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionylamino]-nicotinic acid methyl ester (prepared as in Example 10, 62 mg, 0.16 mmol) in tetrahydrofuran (2 mL) was treated with a solution of lithium hydroxide monohydrate (8 mg, 0.18 mmol) in water (1 mL). The mixture was stirred for 1 h. It was then acidified with 2N aqueous hydrochloric acid and diluted with dichloromethane, washed with saturated sodium chloride solution and dried to afford 6-[(S)-3-cyclopentyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionylamino]-nicotinic acid, (23 mg, 39%) as a white powder: LR-ES-MS m/z calculated for C19H23N3O5 [M]+ 373, observed [M+H]+ 374; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.95-1.97 (m, 11H) 3.79 (s, 3H) 4.01 (d, J=17.9 Hz, 1H) 4.33 (d, J=17.7 Hz, 1H) 4.93 (dd, J=10.9, 4.5 Hz, 1H) 5.18 (s, 1H) 8.12 (d, J=8.5 Hz, 1H) 8.24 (dd, J=8.7, 2.3 Hz, 1H) 8.83 (d, J=2.3 Hz, 1H) 11.18 (s, 1H) 12.81 (br. s., 1H).

Workup

  1. washwashed with saturated sodium chloride solution
  2. customdried

Sources & evidence

ORD record
ord-f93ad563992645aeaac152b803e55076
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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