Ethanolamine → tert-Butyl ((5-(cyclohex-1-en-1-yl)-1-((3-(2-(dimethylamino)-2-oxoethoxy)phenyl) sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

HRID 1051025Notes

Reaction equation

HRID 1051025 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=2)[N:14]([S:16]([C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][CH:29]=2)OCC(O)=O)(=[O:18])=[O:17])[CH:15]=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:36](CN)[OH:37].F[P-](F)(F)(F)(F)F.N1([O:56][C:57](N(C)C)=[N+:58]([CH3:60])[CH3:59])C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[C:30]1([C:13]2[N:14]([S:16]([C:19]3[CH:29]=[CH:28][CH:27]=[C:21]([O:37][CH2:36][C:57]([N:58]([CH3:60])[CH3:59])=[O:56])[CH:20]=3)(=[O:17])=[O:18])[CH:15]=[C:11]([CH2:10][N:8]([CH3:9])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH:12]=2)[CH2:35][CH2:34][CH2:33][CH2:32][CH:31]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 901685832-(3-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(cyclohex-1-en-1-yl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetic acid

Product 1

HCID 90168584tert-Butyl ((5-(cyclohex-1-en-1-yl)-1-((3-(2-(dimethylamino)-2-oxoethoxy)phenyl) sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(3-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(cyclohex-1-en-1-yl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetic acid 8b (69 mg, 0.14 mmol) was dissolved in 15 mL of N, N-dimethylformamide, followed by addition of ethanolamine (16.7 mg, 0.27 mmol), 2-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (104 mg, 0.27 mmol) and N,N-diisopropylethylamine (53 mg, 0.41 mmol), and then the reaction solution was stirred for 1 h. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography with elution system C to obtain the title product tert-butyl ((5-(cyclohex-1-en-1-yl)-1-((3-(2-(dimethylamino)-2-oxoethoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 8c (55 mg, a colorless oily product) in 76% yield.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography with elution system C

Sources & evidence

ORD record
ord-24882ee7ea264e25b244ace7b05b7371
Source dataset
uspto-grants-2016_07
Patent number
US09388133B2

Reaction notes

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