1,2-Dichloroethane → HCID 67587357, compound

HRID 363217Notes

Reaction equation

HRID 363217 reaction equation
[C:1]([O:5][C:6]([CH:8]([C@@H:25]1[CH2:30][CH2:29][CH2:28][CH2:27][NH:26]1)[N:9]([CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[CH2:10][C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[CH3:46][O:47][C:48](=[O:55])[C@H:49]([CH2:51][CH2:52][S:53][CH3:54])[NH2:50].CCN(CC)CC>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([CH:8]([C@@H:25]1[CH2:30][CH2:29][CH2:28][CH2:27][NH:26]1)[N:9]([CH2:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[CH2:10][C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:2])[CH3:3].[CH3:46][O:47][C:48](=[O:55])[C@H:49]([CH2:51][CH2:52][S:53][CH3:54])[NH2:50]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 21307643HCID 21307643, compound

Product 1

HCID 67587357HCID 67587357, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-(t-Butoxycarbonylpiperidin-2(S)-ylmethyl)-N-(1-naphthylmethyl)glycine (2.00 g, 5.0 mmol), dissolved in CH2Cl2 (50 mL), was treated with HOBT (0.743 g, 5.5 mmol), EDC (1.05 g, 5.5 mmol), and methionine methyl ester hydrochloride (1.20 g, 6.0 mmol). The pH was adjusted to 7.5 with Et3N (2.1 mL, 15 mmol) and the mixture was stirred at ambient temperature for 18 h. The mixture was diluted with EtOAc (50 mL), washed with 10% citric acid solution, water, and saturated NaHCO3 solution, brine and dried (MgSO4). Filtration and concentration gave the title compound. 1H NMR (CDCl3); δ8.21 (d, 1H, J=8 Hz), 7.87 (d, 1H, J=8 Hz), 7.80 (d, 1H, J=8 Hz), 7.35-7.6 (m, 5H), 4.33-4.5 (m, 2H), 3.85-4.05 (m, 2H), 3.26 (s, 3H), 3.15-3.33 (m, 2H), 2.62-2.96 (m, 1H), 2.53-2.65 (m, 1H), 2.17 (s, 3H), 1.78-2.05 (m, 4H), 1.15-1.72 (m, 8H), 1.48 (s. 9H).

Workup

  1. washwashed with 10% citric acid solution, water, and saturated NaHCO3 solution, brine
  2. dry with materialdried (MgSO4)
  3. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-a6fd87bc476444efa7855e7ceca07e9f
Source dataset
uspto-grants-1999_02
Patent number
US05872135

Reaction notes

Loading…