1,2-Dichloroethane → HCID 131725245, compound

HRID 489690Notes

Reaction equation

HRID 489690 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9](NC(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.[N:39]1([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:48][C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:41][C@H:40]1[C:49](O)=[O:50].C(Cl)CCl.C1C=CC2N(O)N=[N:69]C=2C=1>CCOC(C)=O.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@@H:9]([NH:69][C:49]([C@@H:40]2[CH2:41][C:42]3[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=3)[CH2:48][N:39]2[C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])=[O:50])[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:6][CH:7]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 664088(3S)-2-((tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 131725244HCID 131725244, compound

Product 1

HCID 131725245HCID 131725245, compoundYield 81.2%

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 (Step b) (0.283 g, 0.54 mmol) and satd anhydrous HCl in EtOAc, followed by Boc-L-TicOH (Advanced ChemTech) (0.18 g, 0.65 mmol), EDC (Advanced ChemTech) (0.155 g, 0.81 mmol), HOBT (Novabiochem) (0.073 g, 0.54 mmol) and TEA (Aldrich) (0.075 mL, 0.54 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 (0.3 g). MS (ESI, pos. ion) m/z: 684 (M+1). Calc'd for C38H42ClN5O5: 683.29.

Workup

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

Sources & evidence

ORD record
ord-91a992f35b63400bad1a6185adf5ea10
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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