Triethylamine → 2-(2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(methanesulfonyloxy)propyl)phenyl)-2-propoxy)tetrahydro pyran

HRID 326935Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([OH:39])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([O:32][CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][O:34]4)([CH3:31])[CH3:30])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:40][S:41](Cl)(=[O:43])=[O:42].CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C@@H:20]([O:39][S:41]([CH3:40])(=[O:43])=[O:42])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[C:29]([O:32][CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][O:34]4)([CH3:31])[CH3:30])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0.1M solution of the alcohol of Step 6 in CH2Cl2 at -40° C. was added 1.3 equiv. of methanesulfonyl chloride and 1.5 equiv. of Et3N and the mixture was stirred 30 min at -40° C. and 1 h at 0° C. Saturated NaHCO3 was then added and the title mesylate was extracted in CH2Cl2, dried over Na2SO4, concentrated and stripped twice with toluene. The residual title compound was used for subsequent reactions without further purification.

Workup

extractionthe title mesylate was extracted in CH2Cl2
dry with materialdried over Na2SO4
concentrationconcentrated
customThe residual title compound was used for subsequent reactions without further purification

Sources & evidence

ORD record: ord-b165d6ba7c464cd6aae81d1e3f3b1d42
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05270324

Reaction notes

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