1,2-Dichloroethane → HCID 22872485, compound

HRID 1779503Notes

Reaction equation

[C:1]([O:5][C:6]([CH:8]([C@@H:17]1[C@@H:21]([CH2:22][CH3:23])[CH2:20][CH2:19][NH:18]1)[N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[CH3:39][O:40][C:41](=[O:48])[C@H:42]([CH2:44][CH2:45][S:46][CH3:47])[NH2:43]>CCOC(C)=O>[CH3:39][O:40][C:41](=[O:48])[C@H:42]([CH2:44][CH2:45][S:46][CH3:47])[NH:43][C:11](=[O:13])[C@@H:10]1[CH2:14][CH2:15][CH2:16][N:9]1[CH:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[C@@H:17]1[C@@H:21]([CH2:22][CH3:23])[CH2:20][CH2:19][NH:18]1

Participants

Conditions

Temperature: 23 °C

Procedure

N-[(tert-Butyloxy)carbonyl-3(S)-ethylpyrrolidin-2(S)-ylmethyl]-proline (0.238 mmol), HOBT (0.048 g, 0.262 mmol), EDC (0.068 g, 0.0357 mmol), and methionine methyl ester hydrochloride (0.048 g, 0.238 mmol) were dissolved in CH2CL2 (10 mL) and stirred at 23° C. for 18 h. EtOAc (100 mL) was added, and the mixture washed with satd NaHCO3 solution, H2O, brine, and dried (MgSO4). Filtration and concentration to dryness gave 0.085 g of title compound. 1H NMR (CD3OD) δ(major rotamer) 4.63 (t, 1H, J=7 Hz), 3.73 (s, 3H), 3.55-3.7 (m, 1H), 3.0-3.5 (m,4H), 2.3-2.7 (m, 5H), 1.9-2.2 (m, 3H), 2.08 (s, 3H), 1.6-1.9 (m, 4H), 1.46 (s, 9H), 1.3-1.45 (m, 2H), 0.92-1.02 (m, 3H).

Workup

washthe mixture washed with satd NaHCO3 solution, H2O, brine
dry with materialdried (MgSO4)
filtrationFiltration and concentration to dryness

Sources & evidence

ORD record: ord-fa17f4afafd7426d967c69d4be9f6f61
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05627202

Reaction notes

Loading…