(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → HCID 68702819, compound

HRID 2261887Notes

Reaction equation

HRID 2261887 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:41])([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:10]([NH:12][NH:13][C:14]([C:16]1[CH:17]=[C:18]([CH:24]=[C:25]([C:27]2([C:32]#[N:33])[CH2:31][CH2:30][CH2:29][CH2:28]2)[CH:26]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>ClC(Cl)C>[C:1]([O:5][C:6]([NH:8][C@:9]([C:10]1[O:15][C:14]([C:16]2[CH:17]=[C:18]([CH:24]=[C:25]([C:27]3([C:32]#[N:33])[CH2:28][CH2:29][CH2:30][CH2:31]3)[CH:26]=2)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:13][N:12]=1)([CH3:41])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 68706681HCID 68706681, compound

Product 1

HCID 68702819HCID 68702819, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of ethyl 3-({2-[(R)-2-tert-butoxycarbonylamino-2-methyl-3-phenylpropanoyl]hydrazino}carbonyl)-5-(1-cyanocyclopentyl)benzoate (0.10 g, 0.18 mmol) and (methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt (0.13 g, 0.54 mmol) in 1.5 mL dichloroethane was heated in the microwave at 120° C. for 8 min. Concentration and flash chromatography (silica gel, 0-45% EtOAc/hexanes) gave ethyl 3-(5-((R)-2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)-5-(1-cyanocyclopentyl)benzoate. 1H NMR (400 MHz, CDCl3) δ 8.57 (app t, J=1.5 Hz, 1H), 8.30 (d, J=1.5 Hz, 2H), 7.29 (m, 3H), 7.08 (m, 2H), 5.11 (br s, 1H), 4.46 (q, J=7.1 Hz, 2H), 3.60 (d, J=13.6 Hz, 1H), 3.44 (d, J=13.6 Hz, 1H), 2.59 (m, 2H), 2.19-1.99 (m, 6H), 1.74 (s, 3H), 1.45 (t, J=7.1 Hz, 3H), 1.43 (s, 9H).

Workup

  1. concentrationConcentration and flash chromatography (silica gel, 0-45% EtOAc/hexanes)

Sources & evidence

ORD record
ord-411ff77554834733ae56c2cced9bafd7
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

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