Water → HCID 59634023, compound

HRID 1615069Notes

Reaction equation

HRID 1615069 reaction equation
Cl.[NH:2]1[CH2:6][C@H:5]([OH:7])[C@@H:4]([OH:8])[CH2:3]1.[OH-].[Na+].CS(O[CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([C:25]([N:27]2[CH2:30][CH:29]([C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][C:42]([CH2:45][CH3:46])=[CH:41][CH:40]=4)=[C:33]([O:47][CH3:48])[CH:32]=3)[CH2:28]2)=[O:26])[CH:20]=1)(=O)=O.O>C(O)CC>[OH:8][C@@H:4]1[C@@H:5]([OH:7])[CH2:6][N:2]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([C:25]([N:27]3[CH2:28][CH:29]([C:31]4[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]5[CH:40]=[CH:41][C:42]([CH2:45][CH3:46])=[CH:43][CH:44]=5)=[C:33]([O:47][CH3:48])[CH:32]=4)[CH2:30]3)=[O:26])[CH:20]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 59633892HCID 59633892, compoundHCID 66787043276862-76-1

Product 1

HCID 59634023HCID 59634023, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

a solution of (3S,4S)-pyrrolidine-3,4-diol monohydrochloride (0.14 g) in 1-propanol (3.0 mL) was added aqueous 4 N NaOH (0.25 mL). The mixture was stirred at RT for 1 hr. To the mixture was added 2-(2-{3-[4-(4-ethylbenzyloxy)-3-methoxyphenyl]azetidine-1-carbonyl}pyridin-4-yloxy)ethyl methanesulfonate (0.1 g) prepared in Example 6 (1). The reaction mixture was stirred at 100° C. for 5 hr. Water was added to the reaction mixture. The precipitated solid was collected on a filter and dried to give the title compound (0.05 g, 50%).

Workup

  1. stirringThe reaction mixture was stirred at 100° C. for 5 hr
  2. customThe precipitated solid was collected on
  3. filtrationa filter
  4. customdried

Sources & evidence

ORD record
ord-bfb11240ea6d42dda2e58bfe750bda5e
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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