Hydrochloric Acid → HCID 86612018, compound

HRID 1454182Notes

Reaction equation

HRID 1454182 reaction equation
[O:1]=[C:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:3][CH2:4][CH2:5][C:6]([Cl:8])=[O:7].CNN(NC)C1(C2C=CC=CC=2)CCC(N)CC1.CC(N=C=NC(C)C)C.ON1C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH3:59][N:60]([CH3:87])[C:61]1([C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)[CH2:66][CH2:65][CH:64]([NH:67]C(=O)CCCC(=O)C2C=CC=CC=2)[CH2:63][CH2:62]1.Cl[Si](C)(C)C>CN(C=O)C.C(OC(=O)C)C.O>[ClH:8].[CH3:59][N:60]([CH3:87])[C:61]1([C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)[CH2:66][CH2:65][CH:64]([NH:67][C:6](=[O:7])[CH2:5][CH2:4][CH2:3][C:2](=[O:1])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:63][CH2:62]1

Participants

12

Reactant 8

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 10340Sodium CarbonateHCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 11618103N-[4-(Dimethylamino)-4-phenylcyclohexyl]-δ-oxobenzenepentanamideHCID 12692055HCID 12692055, compoundHCID 68891964HCID 68891964, compound

Product 1

HCID 86612018HCID 86612018, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

As described for Example 63, 280 mg 5-oxo-5-phenylpentanoylchloride dissolved in 1.6 ml DMF were added to 350 mg of the polar diastereoisomer of N,N-dimethylamino-1-phenylcyclohexane-1,4-diamine, 230 μl N,N-diisopropylcarbodiimide and 200 μg 1-hydroxybenzotriazole (HOBt) at 5° C. while stirring. After three hours at this temperature, the mixture was stirred overnight while heating to room temperature. For working up, one-molar sodium carbonate solution was added (pH>10) and the crude product (794 mg) isolated by extraction with ethylacetate, subsequent drying over sodium sulphate and evaporation. The main fraction of 410 mg obtained by column chromatography on silica gel (4.0×18 cm) with methanol/ethylacetate/n-hexane (V:V:V=1:1:1) was dissolved in 41 ml ethylacetate and was converted into the corresponding hydrochloride of the polar diastereoisomer of 5-oxo-5-phenylpentanoic acid (4-dimethylamino-4-phenylcyclohexyl)amide by adding 19 μl water and 130 μl chlorotrimethylsilane (322 mg white solid).

Workup

  1. stirringthe mixture was stirred overnight
  2. dry with materialsubsequent drying over sodium sulphate and evaporation
  3. customThe main fraction of 410 mg obtained by column chromatography on silica gel (4.0×18 cm) with methanol/ethylacetate/n-hexane (V:V:V=1:1:1)

Sources & evidence

ORD record
ord-a9ea985d3a12409098c46efdc9b669df
Source dataset
uspto-grants-2009_01
Patent number
US07476763B2

Reaction notes

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