Hydrochloric Acid → HCID 11685952, compound

HRID 2099358Notes

Reaction equation

HRID 2099358 reaction equation
[Cl:1][C:2]1[CH:48]=[CH:47][C:5]([CH2:6][C@@H:7]([NH:32][CH2:33][C@@H:34]2[CH2:38][C@@H:37]([OH:39])[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>C(OCC)C>[Cl:1][C:2]1[CH:48]=[CH:47][C:5]([CH2:6][C@H:7]([C:8]([N:10]2[CH:15]3[CH2:16][CH2:17][CH:11]2[CH2:12][CH:13]([N:18]([CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)[C:19]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[O:20])[CH2:14]3)=[O:9])[NH:32][CH2:33][C@@H:34]2[CH2:38][C@@H:37]([OH:39])[CH2:36][NH:35]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86614261HCID 86614261, compound

Product 1

HCID 11685952HCID 11685952, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

0.28 g of tert-butyl (2S,4R)-2-({[(1R)-1-(4-chlorobenzyl)-2-(3-{cyclohexyl[(diethylamino)carbonyl]-amino}-8-azabicyclo[3.2.1]oct-8-yl)-2-oxoethyl]amino}-methyl)-4-hydroxypyrrolidine-1-carboxylate is dissolved in 5 ml of diethyl ether, and then 2.7 ml of 2N hydrochloric acid in diethyl ether are added. Trituration, rinsing with diethyl ether, and filter-drying of the precipitate obtained are carried out, which precipitate is chromatographed on silica gel, elution being carried out with a 90/10/1 mixture of dichloromethane, methanol and aqueous ammonia. 0.18 g of N-[8-(4-chloro-N-{[(2S,4R)-4-hydroxypyrrolidin-2-yl]methyl}-D-phenylalanyl)-8-azabicyclo[3.2.1]oct-3-yl]-N-cyclohexyl-N′,N′-diethylurea is obtained.

Workup

  1. washTrituration, rinsing with diethyl ether
  2. customfilter-drying of the precipitate
  3. customobtained
  4. customwhich precipitate
  5. customis chromatographed on silica gel, elution
  6. additionbeing carried out with a 90/10/1 mixture of dichloromethane, methanol and aqueous ammonia

Sources & evidence

ORD record
ord-21708d7fe26b412cae1a38420fffac23
Source dataset
uspto-grants-2009_08
Patent number
US07569582B2

Reaction notes

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