4-Toluenesulfonyl chloride → HCID 178427793, compound

HRID 707325Notes

Reaction equation

HRID 707325 reaction equation
[OH:1][C@@H:2]1[CH2:5][C@H:4]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:3]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl>[CH3:27][C:17]1[CH:22]=[CH:21][C:20]([S:23]([O:1][C@H:2]2[CH2:3][C@@H:4]([NH:6][C:7]([O:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:16])[CH2:5]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 178523833HCID 178523833, compound2×

Product 1

HCID 178427793HCID 178427793, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzyl (cis-3-hydroxycyclobutyl)carbamate (intermediate 47, 0.3 g, 1.356 mmol), p-toluenesulfonyl chloride (0.284 g, 1.492 mmol), and triethylamine (0.567 ml, 4.07 mmol) in dichloromethane (2.71 ml) was stirred at room temperature for 14 hours. The mixture was diluted with dichloromethane and washed with saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate, rotovapped, and advanced to next step directly.

Workup

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over sodium sulfate

Sources & evidence

ORD record
ord-6f9395cddc904cd1ba75f017e0cd558b
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

Loading…