HCID 86661309, compound → HCID 86661311, compound

HRID 1685075Notes

Reaction equation

HRID 1685075 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([O:13][C:14](=[O:16])[CH3:15])[CH2:10][C@@H:9]1[C:17]1[N:18]=[C:19]([NH:22][C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)=[O:24])[S:20][CH:21]=1)=O)(C)(C)C>Cl.O1CCOCC1>[ClH:33].[Cl:34][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[Cl:33])[CH2:26][NH:25][C:23](=[O:24])[NH:22][C:19]1[S:20][CH:21]=[C:17]([CH:9]2[NH:8][CH2:12][C@H:11]([O:13][C:14](=[O:16])[CH3:15])[CH2:10]2)[N:18]=1

Participants

4

Reactant 1

HCID 86661309HCID 86661309, compound

Product 1

HCID 86661311HCID 86661311, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

The product obtained in Step 2 was dissolved in 4M HCl in 1,4-dioxane (7 mL). After stirring overnight the reaction mixture was concentrated and the residue was crystallized from THF/Et2O to afford Intermediate 58: acetic acid (R)-5-{2-[3-(3,4-dichloro-benzyl)-ureido]-thiazol-4-yl}-pyrrolidin-3-yl ester hydrochloride, as a white solid (224 mg, 52% yield).

Workup

  1. concentrationwas concentrated
  2. customthe residue was crystallized from THF/Et2O

Sources & evidence

ORD record
ord-e5be02bf481f4edeb5f4d52cb623fa2b
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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