1,2-Dichloroethane → HCID 69153176, compound

HRID 489677Notes

Reaction equation

HRID 489677 reaction equation
Cl.[NH2:2][C@H:3]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:4]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][CH2:19][OH:20])[CH2:8][CH2:7]1)=[O:5].CCN(C(C)C)C(C)C.[N:38]1([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:47][C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:40][C@H:39]1[C:48](O)=[O:49].C1C=NC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][C@@H:3]([NH:2][C:48]([C@@H:39]2[CH2:40][C:41]3[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:47][N:38]2[C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[O:49])[C:4]([N:6]2[CH2:11][CH2:10][CH:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][CH2:19][OH:20])[CH2:8][CH2:7]2)=[O:5])=[CH:23][CH:24]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 664088(3S)-2-((tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidHCID 69141554HCID 69141554, compound

Product 1

HCID 69153176HCID 69153176, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the procedure described in Example 1 (Step f) using (2R)-2-amino-3-{4chlorophenyl)-1-(4-[2-(hydroxyethyl)phenyl]-piperidyl}-propan-1-one hydrochloride (Step e) (846 mg, 2.0 mmol), DIEA (0.40 mL, 2.0 mmol), Boc-L-TicOH (Bachem Company) (544 mg, 2.8 mmol), HOAT (Aldrich) (382 mg, 2.8 mmol) and EDC (Aldrich) (544 mg, 2.84 mmol) in DMF (10 mL). Purification by silica gel chromatography (100% EtOAc) provided the title compound as a white foam (739 mg). MS (EST, pos. ion) m/z: 646 (M+1); MS (ESI, neg. ion) m/z: 644 (M−1). Calc'd for C37H44ClN3O5: 645.30.

Workup

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

Sources & evidence

ORD record
ord-bea80a2bd19f41bb9882515e2773efab
Source dataset
uspto-grants-2005_12
Patent number
US06977264B2

Reaction notes

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