Isopropanol → HCID 16660492, compound

HRID 2355248Notes

Reaction equation

[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([C@@H:17]([OH:38])[CH2:18][NH:19][C:20]([CH3:37])([CH3:36])[CH2:21][CH2:22][N:23]3[C:31]4[C:26](=[CH:27][C:28]([C:32](OC)=[O:33])=[CH:29][CH:30]=4)[CH:25]=[CH:24]3)[CH:14]=[CH:15][CH:16]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].C(O)(C(F)(F)F)=O.[CH3:49][CH:50]([OH:52])[CH3:51]>>[C:1]1([S:7]([NH:10][C:11]2[CH:12]=[C:13]([C@@H:17]([OH:38])[CH2:18][NH:19][C:20]([CH3:36])([CH3:37])[CH2:21][CH2:22][N:23]3[C:31]4[C:26](=[CH:27][C:28]([C:32]([O:52][CH:50]([CH3:51])[CH3:49])=[O:33])=[CH:29][CH:30]=4)[CH:25]=[CH:24]3)[CH:14]=[CH:15][CH:16]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 4

HCID 3776Isopropanol

HCID 6422Trifluoroacetic acid

HCID 10942334Sodium Methoxide

HCID 16660494HCID 16660494, compound

Product 1

HCID 16660492HCID 16660492, compound

Procedure

240 mg (0.36 mmol) methyl 1-{3-[(R)-2-[3-(phenylsulphonylamino)-phenyl]-2-hydroxy-ethylamino]-3-methyl-butyl}-1H-indole-5-carboxylate (Example 5) are dissolved in 5 ml 2-propanol and combined with 19 mg (0.36 mmol) sodium methoxide. The mixture is stirred for 17 hours at ambient temperature and then acidified with TFA while cooling with ice. Then the solvent is eliminated in vacuo and the residue is chromatographed on Microsorb C18-reverse-phase [acetonitrile (0.1% TFA)/water (0.13% TFA)=10:90→100:0].

Workup

temperaturewhile cooling with ice
customthe residue is chromatographed on Microsorb C18-reverse-phase [acetonitrile (0.1% TFA)/water (0.13% TFA)=10:90→100:0]

Sources & evidence

ORD record: ord-a711c3ff7f064a76885166ae72ff1932
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754756B2

Reaction notes

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