1,2-Dichloroethane → HCID 69740869, compound

HRID 489692Notes

Reaction equation

HRID 489692 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:30]C(OC(C)(C)C)=O)[C:10](=[O:29])[N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:23]3[CH:27]=[CH:26][NH:25][C:24]3=[O:28])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.Cl.[C:39]([N:46]1[CH2:49][CH:48]([C:50]([OH:52])=O)[CH2:47]1)([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CCOC(C)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([NH:30][C:50]([CH:48]2[CH2:47][N:46]([C:39]([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40])[CH2:49]2)=[O:52])[C:10](=[O:29])[N:11]2[CH2:12][CH2:13][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:23]3[CH:27]=[CH:26][NH:25][C:24]3=[O:28])[CH2:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 131725244HCID 131725244, compound

Product 1

HCID 69740869HCID 69740869, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 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-oxo-2-{4-[2-(2-oxo(4-imidazolinyl))phenyl]-piperidyl)ethyl) (tert-butoxy)carboxamide (Example 18 Step b) (0.227 g, 0.433 mmol) and satd HCl in EtOAc (20 mL), followed by Boc-azetidine-3-carboxylic acid (PepTech Corporation) (0.105 g, 0.52 mmol), EDC (Advanced ChemTech) (0.125 g, 0.65 mmol), HOBT (Novabiochem) (0.058 g, 0.433 mmol) and TEA (Aldrich) (0.058 mL, 0.433 mmol) in CH2Cl2 (10 mL). Purification by silica gel chromatography (100% EtOAc then 1:9 MeOH:EtOAc) provided the title compound as a white foam (0.2 g). MS (ESL pos. ion) m/z: 608 (M+1). Calc'd for C32H38ClN5O5: 607.26.

Workup

  1. customThe title compound was prepared
  2. customPurification by silica gel chromatography (100% EtOAc

Sources & evidence

ORD record
ord-e4f5fb616c5640da86471414118799a3
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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