Ethanol → HCID 67076702, compound
Reaction equation
[NH2:1][C:2]1([C:11]([OH:13])=[O:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.F[C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][C:16]=1[N+:24]([O-])=O.[CH2:27]([OH:29])[CH3:28].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:40][C:41](N(C)C)=O>>[CH2:27]([O:29][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:1][C:2]2([C:11]([OH:13])=[O:12])[CH2:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH2:10]2)=[O:21])=[CH:17][C:16]=1[NH:24][CH2:9][CH2:10][C:2]1[CH:11]=[C:41]([CH3:40])[CH:5]=[CH:4][CH:3]=1)[CH3:28]Participants
Procedure
The synthesis was carried out on 0.15 g of PL Wang resin (1.7 mmol/g). The attachment of 2-amino-indane-2-carboxylic acid and the acylation step using 4-fluoro-3-nitro-benzoic acid were performed as described in example 173. After the acylation step, the resin was shaken with ethanol (5 equivalents) in the presence of sodium bis(trimethylsilyl)amide (5 equivalents) in 3 ml of dimethylacetamide. The resin was washed with DMF, 10% acetic acid/DMF, DMF and finally with DCM. The reduction of the nitro group with tin(II) chloride, sulfonylation with 2,4-dinitro-benzenesulfonyl chloride, alkylation with 2-(3-methylphenyl)-ethanol and removal of the sulfonyl group were performed as described in example 171 and the compound purified by preparative RP HPLC (water/ACN gradient). Yield: 2.4 mg.
Workup
- washThe resin was washed with DMF, 10% acetic acid/DMF, DMF and finally with DCM
- customThe reduction of the nitro group with tin(II) chloride, sulfonylation with 2,4-dinitro-benzenesulfonyl chloride, alkylation with 2-(3-methylphenyl)-ethanol and removal of the sulfonyl group
- customthe compound purified by preparative RP HPLC (water/ACN gradient)
Sources & evidence
- ORD record
- ord-997ac167a45d47aea7d1401d6ec2e0e7
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328071B2
Reaction notes
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