Sulfuryl chloride → HCID 131726119, compound

HRID 2112316Notes

Reaction equation

HRID 2112316 reaction equation
[CH3:1][CH:2]([CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][C@@H:25]2[OH:28])[C@:21]2([CH3:22])[C@@H:16]([CH2:17][C@@H:18]([O:29][CH2:30][CH2:31][N:32]([C:34]4[CH:39]=[CH:38][C:37]([C@H:40]5[CH2:57][C@@:55]6([CH3:56])[C@@H:51]([CH2:52][CH2:53][C@:54]6([OH:61])[C:58]#[C:59][CH3:60])[C@H:50]6[C:41]5=[C:42]5[C:47]([CH2:48][CH2:49]6)=[CH:46][C:45](=[O:62])[CH2:44][CH2:43]5)=[CH:36][CH:35]=4)[CH3:33])[CH2:19][CH2:20]2)[CH2:15][C@H:14]3[O:63][CH2:64]SC)[CH2:11][CH2:10]1)[CH3:8])[C:3]([OH:5])=[O:4].S(Cl)([Cl:70])(=O)=O>ClCCl>[CH3:1][CH:2]([CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][C@@H:25]2[OH:28])[C@:21]2([CH3:22])[C@@H:16]([CH2:17][C@@H:18]([O:29][CH2:30][CH2:31][N:32]([C:34]4[CH:39]=[CH:38][C:37]([C@H:40]5[CH2:57][C@@:55]6([CH3:56])[C@@H:51]([CH2:52][CH2:53][C@:54]6([OH:61])[C:58]#[C:59][CH3:60])[C@H:50]6[C:41]5=[C:42]5[C:47]([CH2:48][CH2:49]6)=[CH:46][C:45](=[O:62])[CH2:44][CH2:43]5)=[CH:36][CH:35]=4)[CH3:33])[CH2:19][CH2:20]2)[CH2:15][C@H:14]3[O:63][CH2:64][Cl:70])[CH2:11][CH2:10]1)[CH3:8])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 131726118HCID 131726118, compound

Product 1

HCID 131726119HCID 131726119, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound of Example 8A is dissolved in dichloromethane; sulfuryl chloride (1.1 eq) is added, and the mixture is stirred at ambient temperature until starting material is consumed. The reaction is quenched by the addition of aqeous sodium bicarbonate; the organic layer is removed, and the aqueous phase is re-extracted with dichloromethane. The combined organic phases are dried (Na2SO4), filtered, and concentrated in vacuo. The crude material is used without further purification.

Workup

  1. customis consumed
  2. customThe reaction is quenched by the addition of aqeous sodium bicarbonate
  3. customthe organic layer is removed
  4. extractionthe aqueous phase is re-extracted with dichloromethane
  5. dry with materialThe combined organic phases are dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material is used without further purification

Sources & evidence

ORD record
ord-6f8d98542ef740baae684fa00119ada6
Source dataset
uspto-grants-2009_04
Patent number
US07521439B2

Reaction notes

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