Lithium Hydroxide → HCID 67506888, compound

HRID 1791923Notes

Reaction equation

HRID 1791923 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[C:24]([Cl:25])=[CH:23][C:22]([C:26]([O:28]CC)=[O:27])=[CH:21][N:20]=3)[CH2:15][CH2:14]2)[CH2:10][C@H:9]1[C:31]([N:33]1[CH2:37][CH2:36][S:35][CH2:34]1)=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.Cl.ClC1C(N2CCN([C@@H]3CN[C@H](C(N4CCSC4)=O)C3)CC2)=NC=C(C(OCC)=O)C=1.[OH-].[Li+]>C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([N:13]2[CH2:14][CH2:15][N:16]([C:19]3[C:24]([Cl:25])=[CH:23][C:22]([C:26]([OH:28])=[O:27])=[CH:21][N:20]=3)[CH2:17][CH2:18]2)[CH2:10][C@H:9]1[C:31]([N:33]1[CH2:37][CH2:36][S:35][CH2:34]1)=[O:32])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 67507330HCID 67507330, compoundHCID 67507426HCID 67507426, compound

Product 1

HCID 67506888HCID 67506888, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-{(2S,4S)-1-tert-Butoxycarbonyl-4-[4-(3-chloro-5-ethoxycarbonyl-2-pyridyl)-1-piperazinyl]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine [product of Example 216 (3), 6.49 g] was dissolved in ethanol (30 mL), and aqueous solution (30 mL) of lithium hydroxide (0.59 g) was added thereto. The mixture was stirred at room temperature for 19 hr and ethanol was evaporated under reduced pressure. The concentrate was washed with ethyl acetate, and 1 mol/L hydrochloric acid was added thereto. The precipitated solid was collected by filtration to give 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(5-carboxy-3-chloro-2-pyridyl)-1-piperazinyl]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine (2.64 g) as a white solid.

Workup

  1. customethanol was evaporated under reduced pressure
  2. washThe concentrate was washed with ethyl acetate, and 1 mol/L hydrochloric acid
  3. additionwas added
  4. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-fe7f0f39209c476a8500b303e5d04434
Source dataset
uspto-grants-2006_07
Patent number
US07074794B2

Reaction notes

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