Triethylamine → HCID 66727301, compound

HRID 1845963Notes

Reaction equation

HRID 1845963 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([S:15]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[CH:24]=[N+:23]([O-])[CH:22]=[CH:21]3)(=[O:17])=[O:16])[C@@H:10]([CH3:29])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)OCC.[C:36]([O:40][C:41]([NH:43][CH2:44][CH2:45][SH:46])=[O:42])([CH3:39])([CH3:38])[CH3:37].C(N(CC)CC)C>ClCCl>[C:36]([O:40][C:41]([NH:43][CH2:44][CH2:45][S:46][C:24]1[C:25]2[C:20](=[CH:19][C:18]([S:15]([N:11]3[CH2:12][CH2:13][CH2:14][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][C@@H:10]3[CH3:29])(=[O:17])=[O:16])=[CH:27][CH:26]=2)[CH:21]=[CH:22][N:23]=1)=[O:42])([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiolHCID 66727336HCID 66727336, compound

Product 1

HCID 66727301HCID 66727301, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

320 mg of (S)-6-(4-tert-butoxycarbonyl-2-methyl-1,4-diazepan-1-ylsulfonyl)isoquinoline 2-oxide was dissolved in dichloromethane, and 0.1 mL of ethyl chlorocarbonate, 0.42 mL of 2-(N-tert-butoxycarbonylamino)ethanethiol, and 0.21 mL of triethylamine were added at 0° C. The reaction solution was stirred at room temperature for 16 hours and then concentrated under reduced pressure, and the obtained crude product was purified by silica gel column chromatography (hexane:acetone=4:1) to obtain 223 mg of the compound of interest as a colorless oil (51%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customthe obtained crude product
  3. customwas purified by silica gel column chromatography (hexane:acetone=4:1)

Sources & evidence

ORD record
ord-6090e760212e40269a29ad6e686bfa9c
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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