Ethyl formate → HCID 57848919, compound

HRID 736803Notes

Reaction equation

HRID 736803 reaction equation
[C:1]([O:5][NH:6][C:7]([C@:9]1([CH3:38])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH:39](OCC)=[O:40].C(N(C(C)C)CC)(C)C>CO>[C:1]([O:5][NH:6][C:7]([C@:9]1([CH3:38])[C@H:14]([NH:15][S:16]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][N:11]([CH:39]=[O:40])[CH2:10]1)=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 81531DiisopropylethylamineHCID 86607899HCID 86607899, compound

Product 1

HCID 57848919HCID 57848919, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
48 °C

Procedure

To a solution of 0.15 g (0.28 mmol) of (3S,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (Example 47, Step 8) in methanol (0.5 mL) was added ethyl formate (3 mL) followed by diisopropylethylamine (0.2 mL, 1.1 mmol). The reaction mixture was stirred at 48° C. for 18 h and concentrated. The residue was purified using silica chromatography, eluting with a gradient of 1-5% MeOH/CH2Cl2 to afford (3S,4R)-N-tert-butoxy-1-formyl -3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (0.092 g, 58%). MS: 569.1 (M+H)+

Workup

  1. concentrationconcentrated
  2. customThe residue was purified
  3. washeluting with a gradient of 1-5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-3736ee6f92084fefadb230ccd587e997
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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