HCID 13721206, compound → HCID 71062635, compound

HRID 528984Notes

Reaction equation

[C:1]1([NH:7]/[N:8]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Si:15]([O:22][CH2:23][C@@H:24]1[CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26][N:25]1[C:34]([C:36]1[CH:37]=[C:38]([CH:46]=[CH:47][C:48]=1[CH:49]=[C:50]([N+]([O-])=O)[CH2:51][CH2:52][CH2:53][CH3:54])[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])=[O:35])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>>[C:42]([O:41][C:39]([C:38]1[CH:46]=[CH:47][C:48]([C:49]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:8][N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:50]=2[CH2:51][CH2:52][CH2:53][CH3:54])=[C:36]([C:34]([N:25]2[C@H:24]([CH2:23][O:22][Si:15]([C:18]([CH3:19])([CH3:21])[CH3:20])([CH3:16])[CH3:17])[CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:35])[CH:37]=1)=[O:40])([CH3:45])([CH3:43])[CH3:44]

Participants

Reactant 2

HCID 13721206HCID 13721206, compound

HCID 86718930HCID 86718930, compound

Product 1

HCID 71062635HCID 71062635, compoundYield 65%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 223E, (E)-ethyl 2-(2-phenylhydrazono)acetate (133 mg, 0.690 mmol) and of (S)-tert-butyl 3-(3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(2-nitrohex-1-enyl)benzoate (420 mg, 0.690 mmol) were converted to the title compound (335 mg, 65%). 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.15-8.06 (m, 2H), 7.51-7.39 (m, 5H), 7.22-6.80 (m, 5H), 5.02-4.98 (m, 1H), 4.39-4.04 (m, 3H), 3.82-3.28 (m, 2H), 3.04-3.00 (m, 1H), 2.90-2.78 (m, 1H), 2.61-2.24 (m, 2H), 1.61 (s, 9H), 1.32-0.90 (m, 7H), 0.77 (s, 9H), 0.59 (t, J=8 Hz, 1.5H), 0.55 (t, J=8 Hz, 1.5H), 0.00 (s, 9H); MS(ESI+) m/z 752.4 (M+H)+.

Sources & evidence

ORD record: ord-7475a0ffce52473e96fe563cd9ff62ca
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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