HCID 11339937, compound → HCID 67048053, compound

HRID 2218516Notes

Reaction equation

[CH3:1][O:2][C:3]([C@H:5]1[N:9]2[C:10](=[O:33])[C:11]([C:31]#[N:32])=[C:12]([CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[C:13]([C:14]3[CH:19]=[CH:18]C=CC=3)=[C:8]2[S:7][CH2:6]1)=[O:4].COC([C@H]1N2C(=O)C(Br)=C(CC3C4C(=CC=CC=4)C=CC=3)C(C3C=CC=CC=3)=C2SC1)=O.COC(C1N2C(=O)C(Br)=C(CC3C4C(=CC=CC=4)C=CC=3)C(C3CC3)=C2SC1)=O>>[CH3:1][O:2][C:3]([CH:5]1[N:9]2[C:10](=[O:33])[C:11]([C:31]#[N:32])=[C:12]([CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[C:13]([CH:14]3[CH2:18][CH2:19]3)=[C:8]2[S:7][CH2:6]1)=[O:4]

Participants

Reactant 3

HCID 11339937HCID 11339937, compound

HCID 11785440HCID 11785440, compound

HCID 67047744HCID 67047744, compound

Product 1

HCID 67048053HCID 67048053, compoundYield 88%

Procedure

By following the procedure described for the preparation of 6a from 5a, 5b (100 mg, 0.21 mmol) gave 6b as a white foam (78 mg, 88%). [α]D−44 (c 1.0, CHCl3); IR λ 3004, 2954, 2360, 2213, 1747, 1644, 1481, 1213, 1164, 792; 1H NMR (400 MHz, CDCl3) 8.12 (d, J=8.2 Hz, 1H), 7.89 (d, J=7.9 Hz, 1H), 7.75 (d, J=8.7 Hz, 1H), 7.62-7.51 (m, 2H), 7.34 (t, 1H), 6,89 (d, J=7.1 Hz, 1H) 5.74 (dd, J=6.7, 2.2 Hz, J=9.8, 2.2 Hz, 1H), 1.27-1.21 (m, 1H), 0.69-0.65 (m, 2H); 0.55-0.53 (m, 2H): 13C NMR (100 MHz, CDCl3) (167.7, 162.9, 158.6, 155.6, 133.8, 132.4, 131.7, 128.9, 127.6, 126.4, 125.9, 125.5, 124.1, 122.8, 115.2, 114.5, 101.7, 63.5, 53.6, 34.8, 31.7, 11.3, 7.7, 7.2; HRMS (FAB+) calcd for C24H21N2O3S 417.1267, obsd 417.1289.

Sources & evidence

ORD record: ord-4827e22666124c659c1df48a720a8f2e
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07411066B2

Reaction notes

Loading…