Hydrochloric Acid → 4-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-L-proline

HRID 2233946Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

A 2 N solution of lithium hydroxide was heated to 70° C. Methyl 4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-L-prolinate (Example 52, 0.081 g, 0.20 mM) in acetonitrile (1.1 ml) and water (0.4 ml) was added to the solution and stirred at 70° C. for ten minutes then ambient temperature for twenty minutes. 1 N Hydrogen chloride was added and a minor impurity was extracted using EtOAc. The aqueous layer was lyophilized to give an orange solid that was purified by HPLC eluting CH3CN/H2O (0.1% TFA). Relevant fractions were collected, concentrated and lyophilized to give the desired product as a light orange solid (0.039 g).

Workup

waitambient temperature for twenty minutes
extractiona minor impurity was extracted
customto give an orange solid
customthat was purified by HPLC
washeluting CH3CN/H2O (0.1% TFA)
customRelevant fractions were collected
concentrationconcentrated

Sources & evidence

ORD record: ord-3fbff6c67c5b4748a08558ccbcba29df
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709503B2

Reaction notes

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