Sulfuryl chloride → HCID 68554334, compound

HRID 456345Notes

Reaction equation

HRID 456345 reaction equation
C(OC([N:8]1[CH2:12][CH:11]([NH:13][C:14](=[O:39])[CH:15]([NH:20][C:21](=[O:38])[CH:22]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[NH:23][C:24]([C:26]2[CH:31]=[N:30][CH:29]=[CH:28][N:27]=2)=[O:25])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH:10]([C:40]([O:42]C(C)(C)C)=[O:41])[CH2:9]1)=O)(C)(C)C.[S:47](Cl)(Cl)(=[O:49])=[O:48]>ClCCl>[C:10]([O:42][C:40]([CH:10]1[CH:11]([NH:13][C:14](=[O:39])[CH:15]([NH:20][C:21](=[O:38])[CH:22]([CH:32]2[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]2)[NH:23][C:24]([C:26]2[CH:31]=[N:30][CH:29]=[CH:28][N:27]=2)=[O:25])[C:16]([CH3:19])([CH3:17])[CH3:18])[CH2:12][N:8]([S:47]([C:35]2[CH:36]=[CH:37][C:32]([CH3:22])=[CH:33][CH:34]=2)(=[O:49])=[O:48])[CH2:9]1)=[O:41])([CH3:40])([CH3:9])[CH3:11]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 68550090HCID 68550090, compound

Product 1

HCID 68554334HCID 68554334, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 23, Part B (100 mg, 0.17 mmol) was dissolved in dichloromethane (1.7 ml). TEA (84 ul, 0.6 mmol) was added followed by the sulfonyl chloride (65.6 mg, 0.34 mmol). The reaction was stirred overnight then loaded onto a silica plug and eluted with ethyl acetate to give the title compound as a white solid (112 mg, 93% yield). MS (APCI) m/z 699 [M+H]+.

Workup

  1. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-99dd1a3d46fc4f139618c6ae0ddc8cb6
Source dataset
uspto-grants-2013_07
Patent number
US08497275B2

Reaction notes

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