Hydrochloric Acid → HCID 86752977, compound

HRID 481791Notes

Reaction equation

C1(C)C=CC(S([N:9]2[C@@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C@H:10]2[C:18]([O:20][CH3:21])=[O:19])=O)=CC=1.[ClH:23]>CO>[ClH:23].[NH2:9][C@H:10]([C@H:11]([Cl:23])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]([O:20][CH3:21])=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

Into a 50-mL round-bottomed flask equipped with a magnetic stir bar were placed 0.315 g (1.0 mmol) (2S,3S)-(-)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine (prepared according to Example 1) and 10 mL freshly distilled methanol. The solution was cooled to 0° C. and 2 mL of 5N HCl were added dropwise. The reaction mixture was brought to room temperature and stirred for 1 h. The solvent was removed on a rotary evaporator, the residue was dissolved in 5 mL of H2O and washed with ether (3×10 mL). The aqueous solution was concentrated on a rotary evaporator and dried overnight using a high vacuum pump to give the titled compound (0.178 g, 81%): mp 160°-162° C.; [α]D20 -45.47° (c 1.7, MeOH); IR (KBr): 3300-2600, 1765, 1580, 1485, 1330, 1280, 1150, 1055 cm-1 ; 1H NMR (DMSO-d6) δ3.52 (s, 3H, CH3), 4.69 (d, J=7.8 Hz, 1H, N--CH), 5.54 (d, J=7.8 Hz, 1H, O--CH), 7.49-7.39 (m, 5H, aromatic), 9.15 (bs, 3H, NH); 13C NMR (DMSO-d6) δ52.8, 58.2, 60.3, 127.6, 128.5, 129.2, 135.0, 166.0. Anal. Calcd for C10H13Cl2NO2 : C, 48.02; H, 5.26. Found: C, 47.93; H, 5.30.

Workup

customInto a 50-mL round-bottomed flask equipped with a magnetic stir bar
customwas brought to room temperature
customThe solvent was removed on a rotary evaporator
dissolutionthe residue was dissolved in 5 mL of H2O
washwashed with ether (3×10 mL)
concentrationThe aqueous solution was concentrated on a rotary evaporator
customdried overnight

Sources & evidence

ORD record: ord-da11808327d84c1f8e0529caa72ee8f2
Source dataset: uspto-grants-1998_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05789599

Reaction notes

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