Sulfuryl chloride → HCID 86641296, compound

HRID 1950743Notes

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

Reactant 2

HCID 24648Sulfuryl chloride

HCID 86641297HCID 86641297, compound

Product 1

HCID 86641296HCID 86641296, compound

Procedure

Compound 47 neat (519.2 mg, 1.054 mmol) was cooled in an ice/water bath and sulfuryl chloride (128 μL, 1.579 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 48 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), 2.90 (q, J=7.3, 2H), 4.14-4.24 (m, 8H), 5.82 (s, 2H).

Workup

customAfter removal of the excess sulfuryl chloride in vacuo
customthe crude acid chloride 48 was used directly in the next step without further purification

Sources & evidence

ORD record: ord-9de32b717fb940d59bc55b984b7e9168
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404664B2

Reaction notes

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