HCID 22141400, compound → HCID 69968568, compound
Reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@H:10]([NH2:18])[CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.I[CH2:20][C@@H:21]([C:30]1[C:31](Cl)=[C:32]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:33]=[CH:34][CH:35]=1)[O:22][Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25].BrCC(C1C=CC([Cl:52])=C(NS(C)(=O)=O)C=1)=O>>[CH2:24]([Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[O:22][C@H:21]([C:30]1[CH:35]=[CH:34][C:33]([Cl:52])=[C:32]([NH:36][S:37]([CH3:40])(=[O:39])=[O:38])[CH:31]=1)[CH2:20][NH:18][CH:10]([C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH3:25]Participants
Procedure
The title compound was prepared by coupling (R)-α-(1,3-benzodioxol-5-yl)benzeneethanamine (preparation described in Step B of Example 60) with (R)-N-[3-[2-iodo-1-[(triethylsilyl)oxy]ethyl]-2-chlorophenyl]methanesulfonamide (prepared from 2-bromo-1-[4-chloro-3-[(methylsulfonyl)amino]phenyl]ethanone, preparation described in Example 69, utilizing the procedures described in step A-C of Example 19) following the procedure described in steps D and E of Example 19 with the following modifications. 1) Chromatography on silica gel using 25% EtOAc/hexane yielded (R), (R)-N-[5-[1-(triethylsilyl)oxy-2-[[1-(1,3-benzodioxol-5-yl)-2-phenylethyl]amino]ethyl]-2-chlorophenyl]methanesulfonamide. 2) In step E the title compound was eluted from silica gel using 1:1 EtOAc/hexane prior to final preparative HPLC purification (see Example 1 for HPLC protocol) eluting with 52% solvent B.
Workup
- customThe title compound was prepared
Sources & evidence
- ORD record
- ord-4c8a3a9cf5794d25a2e3b61a7aae2c41
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05776983
Reaction notes
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