HCID 86614262, compound → HCID 11635499, compound

HRID 2099361Notes

Reaction equation

HRID 2099361 reaction equation
[Cl:1][C:2]1[CH:44]=[CH:43][C:5]([CH2:6][C@@H:7]([NH:32][CH2:33][CH2:34][NH:35]C(=O)OC(C)(C)C)[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>[ClH:1].[NH2:35][CH2:34][CH2:33][NH:32][C@@H:7]([C:8]([N:10]1[CH:15]2[CH2:16][CH2:17][CH:11]1[CH2:12][CH:13]([N:18]([CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1)[C:19]([N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])=[O:20])[CH2:14]2)=[O:9])[CH2:6][C:5]1[CH:43]=[CH:44][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 86614262HCID 86614262, compound

Product 1

HCID 11635499HCID 11635499, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

0.14 g of tert-butyl (2-{[(1R)-1-(4-chlorobenzyl)-2-(3-{cyclohexyl[(diethylamino)carbonyl]amino}-8-azabicyclo[3.2.1]oct-8-yl)-2-oxoethyl]amino}ethyl)-carbamate is placed in 1.1 ml of 2N hydrochloric acid in diethyl ether. The reaction medium is stirred at ambient temperature for 1 h. Trituration, rinsing with diethyl ether and filter-drying of the precipitate obtained are carried out. The salt thus obtained is chromatographed on silica gel, elution being carried out with a 98/2/0.2 and then 95/5/0.5 mixture of dichloromethane, methanol and aqueous ammonia. 0.05 g of N-{8-[N-(2-aminoethyl)-4-chloro-D-phenylalanyl]-8-azabicyclo[3.2.1]oct-3-yl}-N-cyclohexyl-N′,N′-diethylurea hydrochloride is obtained.

Workup

  1. washTrituration, rinsing with diethyl ether
  2. customfilter-drying of the precipitate
  3. customobtained
  4. customThe salt thus obtained
  5. customis chromatographed on silica gel, elution
  6. addition95/5/0.5 mixture of dichloromethane, methanol and aqueous ammonia

Sources & evidence

ORD record
ord-376df4e1a6b44261bdd9d737c72d72f5
Source dataset
uspto-grants-2009_08
Patent number
US07569582B2

Reaction notes

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