HCID 86614263, compound → HCID 68829890, compound

HRID 2099365Notes

Reaction equation

HRID 2099365 reaction equation
[Cl:1][C:2]1[CH:52]=[CH:51][C:5]([CH2:6][C@@H:7]([NH:32][CH2:33][C@H:34]2[CH2:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:36][N:35]2C(OC(C)(C)C)=O)[C:8]([N:10]2[CH:15]3[CH2:16][CH2:17][CH:11]2[CH2:12][CH:13]([N:18]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[O:20])[CH2:14]3)=[O:9])=[CH:4][CH:3]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@H:7]([C:8]([N:10]2[CH:11]3[CH2:17][CH2:16][CH:15]2[CH2:14][CH:13]([N:18]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[C:19]([N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])=[O:20])[CH2:12]3)=[O:9])[NH:32][CH2:33][C@H:34]2[CH2:43][C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:36][NH:35]2)=[CH:51][CH:52]=1

Participants

4

Reactant 1

HCID 86614263HCID 86614263, compound

Product 1

HCID 68829890HCID 68829890, compoundYield 47.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

0.29 g of tert-butyl (3R)-3-({[(1R)-1-(4-chlorobenzyl)-2-(3-{cyclohexyl[(diethylamino)carbonyl]-amino}-8-azabicyclo[3.2.1]oct-8-yl)-2-oxoethyl]amino}-methyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate is placed in 1.1 ml of 4N hydrochloric acid in dioxane. The reaction medium is stirred at ambient temperature for 1 h. After hydrolysis with a 1N aqueous sodium hydroxide solution, extraction is carried out with dichloromethane until the aqueous phase is completely depleted. Drying over MgSO4 and concentration to dryness are carried out. The crude obtained is chromatographed on silica gel, elution being carried out with a 98/2 mixture of dichloromethane and methanol. 0.12 g of N-(8-{4-chloro-N-[(3R)-1,2,3,4-tetrahydroisoquinolin-3-ylmethyl]-D-phenylalanyl}-8-azabicyclo[3.2.1]oct-3-yl)-N-cyclohexyl-N′,N′-diethylurea is obtained.

Workup

  1. customAfter hydrolysis
  2. extractionwith a 1N aqueous sodium hydroxide solution, extraction
  3. dry with materialDrying over MgSO4 and concentration to dryness
  4. customThe crude obtained
  5. customis chromatographed on silica gel, elution
  6. additionbeing carried out with a 98/2 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-e43eaa82834e4431aa0cf0cc60371c4c
Source dataset
uspto-grants-2009_08
Patent number
US07569582B2

Reaction notes

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