Potassium Carbonate → HCID 69067118, compound

HRID 899139Notes

Reaction equation

[CH2:1]([N:8]([S:16]([CH3:19])(=[O:18])=[O:17])[CH2:9][CH2:10]OS(C)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O:24][C:25]([N:27]1[CH2:34][CH:33]2[O:35][CH:29]([CH2:30][NH:31][CH2:32]2)[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C([O-])([O-])=O.[K+].[K+].[Br-].[Li+]>C(#N)C>[C:20]([O:24][C:25]([N:27]1[CH2:28][CH:29]2[O:35][CH:33]([CH2:32][N:31]([CH2:10][CH2:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[S:16]([CH3:19])(=[O:18])=[O:17])[CH2:30]2)[CH2:34]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 60 °C

Procedure

A suspension of methanesulfonic acid 2-(benzyl-methanesulfonyl-amino)-ethyl ester (4 g, 0.0130 mol; from step (ii) above), 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (3 g, 0.013 mol; see WO 01/28992)), dry K2CO3 (3.6 g, 0.026 mol) and lithium bromide (2.2 g, 0.026 mol) in dry acetonitrile (50 ml) was stirred at 60° C. overnight under N2. The reaction mixture was filtered and filtrate was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using 4% methanol in dichloromethane as eluent to yield (5 g) of the sub-title compound as a solid.

Workup

filtrationThe reaction mixture was filtered
concentrationfiltrate was concentrated under reduced pressure
customThe residue was purified by column chromatography over silica gel using 4% methanol in dichloromethane as eluent

Sources & evidence

ORD record: ord-f3e79813b2c84c43a41869222c81c0aa
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07354917B2

Reaction notes

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