Methyl iodide → HCID 69886225, compound

HRID 49523Notes

Reaction equation

HRID 49523 reaction equation
CI.[CH2:3]1CCN2C(=NCCC2)CC1.[OH:14][C@@H:15]1[CH2:19][C@H:18]([OH:20])[C@H:17]([CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][C:27]([NH:29][S:30]([CH3:33])(=[O:32])=[O:31])=[O:28])[C@H:16]1/[CH:34]=[CH:35]/[C@@H:36]([OH:42])[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>CC(C)=O.CCOC(C)=O>[OH:14][C@@H:15]1[CH2:19][C@H:18]([OH:20])[C@H:17]([CH2:21]/[CH:22]=[CH:23]\[CH2:24][CH2:25][CH2:26][C:27]([N:29]([CH3:3])[S:30]([CH3:33])(=[O:32])=[O:31])=[O:28])[C@H:16]1/[CH:34]=[CH:35]/[C@@H:36]([OH:42])[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 25044723HCID 25044723, compound

Product 1

HCID 69886225HCID 69886225, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl iodide (38 μL, 0.61 mmol) and DBU (45 μL, 0.30 mmol) were added to a solution of N-{(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((S)-(E)-3-hydroxyoct-1-enyl)cyclopentyl]hept-5-enoyl}methanesulfonamide (44 mg, 0.10 mmol) in acetone (1.5 mL). After stirring for 2.5 h at room temperature, the reaction was diluted with EtOAc, washed with water (2×) and brine then concentrated in vacuo to afford the title compound. See FIG. 1.

Workup

  1. washwashed with water (2×) and brine
  2. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-7554628260ef42abad6b46ff21b8ca04
Source dataset
uspto-grants-2004_03
Patent number
US06706755B2

Reaction notes

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