1,2-Dichloroethane → HCID 131725243, compound

HRID 489687Notes

Reaction equation

HRID 489687 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:31]C(OC(C)(C)C)=O)[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]3[CH:28]=[CH:27][N:26]([CH3:29])[C:25]3=[O:30])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.Cl.[N:40]1([C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])[CH2:49][C:48]2[C:43](=[CH:44]C=CC=2)[CH2:42][C@H:41]1[C:50]([OH:52])=O.[CH:60]1[CH:65]=NC2N(O)N=NC=2[CH:61]=1.C(Cl)CCl>CCOC(C)=O.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:31][C:50]([C@@H:41]2[CH2:42][C:43]3[C:48](=[CH:61][CH:60]=[CH:65][CH:44]=3)[CH2:49][N:40]2[C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[O:52])[C:10]([N:12]2[CH2:13][CH2:14][CH:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:24]3[CH:28]=[CH:27][N:26]([CH3:29])[C:25]3=[O:30])[CH2:16][CH2:17]2)=[O:11])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 181649HOAtHCID 664088(3S)-2-((tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 131725242HCID 131725242, compound

Product 1

HCID 131725243HCID 131725243, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared according to the procedure described in Example 10 (Step b) using N-((1R)-1-[(4-chlorophenyl)methyl]-2-{4-[2-(3-methyl-2-oxo(4-imidazolinyl))-phenyl]piperidyl}-2-oxoethyl)(tert-butoxy)carboxamide (Step b) (0.237 g, 0.44 mmol) and satd anhydrous HCl in EtOAc, followed by Boc-L-TicOH (Advanced ChemTech) (0.123 g, 0.44 mmol), HOAT (Aldrich) (0.06 g, 0.44 mmol), TEA (Aldrich) (0.06 mL, 0.44 mmol) and EDC (Advanced ChemTech) (0.126 g, 0.66 mmol) in DMF (10 mL). Purification by silica gel chromatography (EtOAc then 1:9 MeOH:EtOAc) provided the title compound as a pale yellow foam (0.12 g). MS (ESI, pos. ion) m/z: 698 (M+1). Calc'd for C39H44ClN5O5: 697.30.

Workup

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography (EtOAc

Sources & evidence

ORD record
ord-d6006ddf5df342e58215e3d3a5cf5a57
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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