Sulfuryl chloride → HCID 86641296, compound

HRID 1841913Notes

Reaction equation

HRID 1841913 reaction equation
[C:1](=[O:30])([O:5][CH2:6][O:7][C:8](=[O:29])[CH2:9][CH2:10][CH2:11][CH:12]([P:21]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22])[P:13]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])=[O:14])SCC.S(Cl)([Cl:34])(=O)=O>>[CH2:16]([O:15][P:13]([CH:12]([P:21]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22])[CH2:11][CH2:10][CH2:9][C:8]([O:7][CH2:6][O:5][C:1]([Cl:34])=[O:30])=[O:29])([O:18][CH2:19][CH3:20])=[O:14])[CH3:17]

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 86641297HCID 86641297, compound

Product 1

HCID 86641296HCID 86641296, compound

Procedure

Compound 56 neat (519.2 mg, 1.054 mmol) was cooled in an ice/water bath and sulfuryl chloride (128 μL, 1.58 mmol) was carefully added. The reaction mixture was allowed to warm to room temperature and was stirred overnight. After removal of the excess sulfuryl chloride in vacuo, the crude acid chloride 57 was used directly in the next step without further purification. 1HNMR (400 MHz, CDCl3): δ 1.35 (t, J=7.0, 12H), 1.86-2.06 (m, 4H), 2.28 (tt, J=23.8, 6.2, 1H), 2.45 (t, J=7.0, 2H), 4.14-4.24 (m, 8H), 5.82 (s, 2H). 31P NMR (162 MHz, CDCl3) δ 24.34 (s, 2P)

Workup

  1. customAfter removal of the excess sulfuryl chloride in vacuo
  2. customthe crude acid chloride 57 was used directly in the next step without further purification

Sources & evidence

ORD record
ord-ee37bd2f63c045eea1190f05ba281759
Source dataset
uspto-grants-2015_02
Patent number
US08946144B2

Reaction notes

Loading…