Acetonitrile → HCID 68442494, compound

HRID 2246958Notes

Reaction equation

HRID 2246958 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12]([S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C@@H:11]([CH2:42][C@@H:43](OS(C)(=O)=O)[CH:44]([CH3:46])[CH3:45])[CH2:10]2)=[CH:5][CH:4]=1.[C:52](#[N:54])C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]2[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[O:25][CH2:24][CH2:23][N:22]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:21]=4[CH:31]=3)[CH2:13][N:12]([S:32]([C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=3)(=[O:33])=[O:34])[C@@H:11]([CH2:42][C@@H:43]([CH:44]([CH3:46])[CH3:45])[C:52]#[N:54])[CH2:10]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 86621624HCID 86621624, compound

Product 1

HCID 68442494HCID 68442494, compound

Reagents, catalysts & solvents 1

HCID 165872Tetrabutylammonium CyanideCatalyst

Procedure

Similar to example 19c, 370 mg of methanesulfonic acid (R)-1-[(2R,4R,5R)-4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-ylmethyl]-2-methyl-propyl ester in the presence of 275 mg of tetrabutylammonium cyanide in acetonitrile are used to afford the title compound as a yellow oil. Rf=0.30 (EtOAc-heptane 1:1); Rt=5.38.

Sources & evidence

ORD record
ord-50cd10ce53a3424788b7d67955296be6
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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