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

HRID 865482Notes

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-4c9350abd4eb4da787367e9ff7e3b513
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05565473

Reaction notes

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