HCID 86614260, compound → HCID 68829063, compound

HRID 2099350Notes

Reaction equation

HRID 2099350 reaction equation
[Cl:1][C:2]1[CH:41]=[CH:40][C:5]([CH2:6][C@@H:7]([NH:32]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>[Cl:1][C:2]1[CH:3]=[CH:4][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]([CH2:22][CH3:23])[CH2:24][CH3:25])=[O:20])[CH2:14]3)=[O:9])[NH2:32])=[CH:40][CH:41]=1

Participants

4

Reactant 1

HCID 86614260HCID 86614260, compound

Product 1

HCID 68829063HCID 68829063, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 3283Diethyl EtherSolvent2×

Procedure

1.42 g of tert-butyl [(1R)-1-(4-chlorobenzyl)-2-(3-{cyclohexyl[(diethylamino)carbonyl]amino}-8-azabicyclo[3.2.1]oct-8-yl)-2-oxoethyl]carbamate are placed in 12 ml of 2N hydrochloric acid in diethyl ether. The reaction medium is stirred at ambient temperature for 3 h. 5 ml of 2N hydrochloric acid in diethyl ether are added and stirring is maintained for 16 h. After evaporation to dryness, the crude obtained is chromatographed on silica gel, elution being carried out with a 95/5/0.5 mixture of dichloromethane, methanol and aqueous ammonia. 1.03 g of N-[8-(4-chloro-D-phenylalanyl)-8-azabicyclo[3.2.1]oct-3-yl]-N-cyclohexyl-N′,N′-diethylurea are obtained.

Workup

  1. stirringstirring
  2. temperatureis maintained for 16 h
  3. customAfter evaporation to dryness
  4. customthe crude obtained
  5. customis chromatographed on silica gel, elution
  6. additionbeing carried out with a 95/5/0.5 mixture of dichloromethane, methanol and aqueous ammonia

Sources & evidence

ORD record
ord-f521f4a7c96f4fa39e9c7c9d8392b7e1
Source dataset
uspto-grants-2009_08
Patent number
US07569582B2

Reaction notes

Loading…