(S)-2-(phenoxymethyl)morpholine → 7-Nitro-3-{[(2S)-2-(phenoxymethyl)morpholin-4-yl]sulfonyl}-1H-indole-2-carboxylic acid
Reaction equation
BrC1C=C2C(=CC=1)N(S(C1C=CC=CC=1)(=O)=O)C(C(OCC)=O)=C2S(Cl)(=O)=O.Cl[S:30]([C:33]1[C:41]2[C:36](=[C:37]([N+:42]([O-:44])=[O:43])[CH:38]=[CH:39][CH:40]=2)[N:35](S(C2C=CC=CC=2)(=O)=O)[C:34]=1[C:54]([O:56]CC)=[O:55])(=[O:32])=[O:31].[O:59]([CH2:66][C@H:67]1[O:72][CH2:71][CH2:70][NH:69][CH2:68]1)[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>>[N+:42]([C:37]1[CH:38]=[CH:39][CH:40]=[C:41]2[C:36]=1[NH:35][C:34]([C:54]([OH:56])=[O:55])=[C:33]2[S:30]([N:69]1[CH2:70][CH2:71][O:72][C@H:67]([CH2:66][O:59][C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)[CH2:68]1)(=[O:31])=[O:32])([O-:44])=[O:43]Participants
4
Reactant 3
Product 1
Procedure
Following the procedure described in Steps B and C of Example 2, replacing in Step B ethyl 5-bromo-3-(chlorosulfonyl)-1-(phenylsulfonyl)-1H-indole-2-carboxylate with ethyl 3-(chlorosulfonyl)-7-nitro-1-(phenylsulfonyl)-1H-indole-2-carboxylate and replacing morpholine with (S)-2-(phenoxymethyl)morpholine from Step A of Example 23, the title compound was obtained. ESI+MS: 461.9 [M+H]+.
Sources & evidence
- ORD record
- ord-5362104c97c44ff2ae1429d4d3db2b6b
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07560546B2
Reaction notes
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