4-Methoxybenzenesulfonyl chloride → HCID 69310689, compound

HRID 751469Notes

Reaction equation

HRID 751469 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([C:13](=[O:23])[NH:14][CH:15]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17][CH:16]1[OH:22])[CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:4])([CH3:3])[CH3:2].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>ClCCCl>[C:1]([O:5][C:6](=[O:24])[NH:7][C@H:8]([C:13](=[O:23])[NH:14][CH:15]1[CH2:21][CH2:20][CH2:19][N:18]([S:33]([C:30]2[CH:29]=[CH:28][C:27]([O:26][CH3:25])=[CH:32][CH:31]=2)(=[O:35])=[O:34])[CH2:17][CH:16]1[OH:22])[CH2:9][CH:10]([CH3:12])[CH3:11])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 12076054HCID 12076054, compound2×

Product 1

HCID 69310689HCID 69310689, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

[(S)-1-(3-Hydroxy-azepan-4-ylcarbamoyl)-3-methyl-butyl]-carbamic acid-tert-butyl ester (compound 2g, 0.8 g, 2.33 mmol) was dissolved in 1,2-dichloroethane (DCE, 20 ml). Then, morpholinemethyl polystyrene resin beads (1.26 g, 3.7 mmol/g, Nova) were added and the solution was shaken for 5 minutes. Then, p-methoxybenzenesulfonyl chloride (0.48 g, 2.33 mmol) was dissolved in DCE (10 ml), and this solution was added to the reaction mixture. The reaction was shaken overnight, filtered, washed with DCE (2×10 ml), then CH2Cl2 (10 ml). The combined organics were concentrated in vacuo, and used in the next reaction without further purification: M+H+=514.2.

Workup

  1. additionwere added
  2. additionthis solution was added to the reaction mixture
  3. stirringThe reaction was shaken overnight
  4. filtrationfiltered
  5. washwashed with DCE (2×10 ml)
  6. concentrationThe combined organics were concentrated in vacuo
  7. customused in the next reaction without further purification

Sources & evidence

ORD record
ord-c369d8bcc5014b5d9cbe3305d4679179
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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