4-Methyloxybenzyl chloride → (S)-1-(4-methoxybenzyl)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione

HRID 2191232Notes

Reaction equation

HRID 2191232 reaction equation
CN1C2C(=CC(S(N3CCC[C@H]3COC3C=CC=CC=3)(=O)=O)=CC=2)C(=O)C1=O.[O:29]([CH2:36][C@@H:37]1[CH2:40][CH2:39][N:38]1[S:41]([C:44]1[CH:45]=[C:46]2[C:50](=[CH:51][CH:52]=1)[NH:49][C:48](=[O:53])[C:47]2=[O:54])(=[O:43])=[O:42])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[CH3:55][O:56][C:57]1[CH:64]=[CH:63][C:60]([CH2:61]Cl)=[CH:59][CH:58]=1>>[CH3:55][O:56][C:57]1[CH:64]=[CH:63][C:60]([CH2:61][N:49]2[C:50]3[C:46](=[CH:45][C:44]([S:41]([N:38]4[CH2:39][CH2:40][C@H:37]4[CH2:36][O:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)(=[O:43])=[O:42])=[CH:52][CH:51]=3)[C:47](=[O:54])[C:48]2=[O:53])=[CH:59][CH:58]=1

Participants

4

Reactant 3

HCID 699934-Methyloxybenzyl chlorideHCID 52888501-Methyl-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dioneHCID 11624920(S)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione

Product 1

HCID 11684618(S)-1-(4-methoxybenzyl)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dioneYield 50%

Procedure

(S)-1-(4-Methoxybenzyl)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione (18c) was prepared according to the same procedure for compound 11a, except using compound 17 and 4-methoxybenzyl chloride, and purified with hexanes-ether (1:2) to afford 62 mg (50%) of 18c as an orange solid, mp 159.8-161.5° C. 1H NMR (300 MHz, CDCl3) δ 8.04 (s, 1H), 7.96 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.25 (m, 4H), 6.97-6.87 (m, 4H), 6.80 (d, J=7.8 Hz, 2H), 4.87 (s, 2H), 4.45 (m, 2H), 4.11 (m, 2H), 3.84 (m, 2H), 3.81 (s, 3H), 2.32 (m, 2H). Anal. Calcd for C26H24N2O6S: C, 63.40, H, 4.91; N, 5.69. Found: C, 63.65, H, 4.93; N, 5.59.

Workup

  1. custom(S)-1-(4-Methoxybenzyl)-5-(2-phenoxymethyl-azetidine-1-sulfonyl)-1H-indole-2,3-dione (18c) was prepared
  2. custompurified with hexanes-ether (1:2)

Sources & evidence

ORD record
ord-86b92b6b61d74a13b4bb105d71179b03
Source dataset
uspto-grants-2012_12
Patent number
US08329686B2

Reaction notes

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