Diisopropylethylamine → HCID 86614260, compound

HRID 2099349Notes

Reaction equation

HRID 2099349 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH:3]([N:9]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:11])[CH2:2]2.[CH3:23][C:24]([O:27][C:28]([NH:30][C@@H:31]([C:40](O)=[O:41])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=1)=[O:29])([CH3:26])[CH3:25].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C>ClCCl>[Cl:39][C:36]1[CH:35]=[CH:34][C:33]([CH2:32][C@@H:31]([NH:30][C:28](=[O:29])[O:27][C:24]([CH3:26])([CH3:23])[CH3:25])[C:40]([N:8]2[CH:1]3[CH2:7][CH2:6][CH:5]2[CH2:4][CH:3]([N:9]([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[C:10]([N:12]([CH2:13][CH3:14])[CH2:15][CH3:16])=[O:11])[CH2:2]3)=[O:41])=[CH:38][CH:37]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 7018791N-Boc-4-chloro-D-phenylalanineHCID 68828546HCID 68828546, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86614260HCID 86614260, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.8 g of N-8-azabicyclo[3.2.1]oct-3-yl-N-cyclohexyl-N′,N′-diethylurea are dissolved in 70 ml of dichloromethane in the presence of 1.75 g of Boc-D-4-chlorophenylalanine, of 0.79 g of hydroxybenzotriazole, of 1.12 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and of 1.02 ml of diisopropylethylamine. The mixture is stirred at ambient temperature for 16 h. After evaporation to dryness, the residue is hydrolysed and extracted with ethyl acetate until the aqueous phase is completely depleted. The organic phase is washed with H2O and then with a saturated aqueous sodium chloride solution. After drying over MgSO4 and concentration to dryness, the crude is chromatographed on silica gel, elution being carried out with a 99/1 mixture of dichloromethane and methanol, to give 1.42 g of tert-butyl [(1R)-1-(4-chlorobenzyl)-2-(3-{cyclohexyl[(di-ethylamino)carbonyl]amino}-8-azabicyclo[3.2.1]oct-8-yl)-2-oxoethyl]carbamate.

Workup

  1. customAfter evaporation to dryness
  2. extractionextracted with ethyl acetate until the aqueous phase
  3. washThe organic phase is washed with H2O
  4. dry with materialAfter drying over MgSO4 and concentration to dryness
  5. customthe crude is chromatographed on silica gel, elution
  6. additionbeing carried out with a 99/1 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-5da3b755eff6486fb0b96fd4586a8c83
Source dataset
uspto-grants-2009_08
Patent number
US07569582B2

Reaction notes

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