(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → HCID 68668979, compound

HRID 1161953Notes

Reaction equation

HRID 1161953 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]([CH3:36])([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:10]([NH:12][NH:13][CH2:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][CH3:26])[C:19](=[O:27])[C:18]1=[O:28])=O)=[O:11])=[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:11][C:14]([CH2:15][N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][CH3:26])[C:19](=[O:27])[C:18]2=[O:28])=[N:13][N:12]=1)([CH3:36])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 68669056HCID 68669056, compound

Product 1

HCID 68668979HCID 68668979, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 1-((2-((R)-2-tert-butoxycarbonylamino-2-methyl-3-phenylpropanoyl)hydrazino)acetyl)-4-butylpiperazine-2,3-dione from Step A (80 mg, 0.16 mmol) and (methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt (152 mg, 0.64 mmol) in 1.6 mL dichloroethane was heated in the microwave at 120° C. for 8 min. Concentration and flash chromatography (silica gel, 80-100% EtOAc/hexanes) gave 1-((5-(2-tert-butoxycarbonylamino-1-phenylpropan-2-yl)-1,3,4-oxadiazol-2-yl)methyl)-4-butylpiperazine-2,3-dione. 1H NMR (CDCl3) δ 7.30 (m, 3H), 7.05 (m, 2H), 4.92 (m, 3H), 3.61 (m, 2H), 3.55 (m, 2H), 3.48 (m, 3H), 3.30 (d, 1H, J=13.6 Hz), 1.60 (s, 3H), 1.57 (m, 2H), 1.40 (s, 9H), 1.35 (m, 2H), 0.94 (t, 3H, J=7.3 Hz).

Workup

  1. concentrationConcentration and flash chromatography (silica gel, 80-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8cf73efeacdd477ca9d521bf1d663449
Source dataset
uspto-grants-2010_10
Patent number
US07820674B2

Reaction notes

Loading…