Thionyl Chloride → HCID 11626155, compound

HRID 251877Notes

Reaction equation

HRID 251877 reaction equation
O=[C:2]1[O:6][C@H](C(Cl)(Cl)Cl)[O:4][CH:3]1[CH2:11][C:12]([OH:14])=O.S(Cl)(Cl)=O.FC(F)(F)C(O)=O.[Cl:26][C:27]1[CH:28]=[C:29]2[C:34](=[C:35]([Cl:37])[CH:36]=1)[CH2:33][N:32]([CH:38]1[CH2:40][CH2:39]1)[CH2:31][C@H:30]2[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[NH2:47]>O.C(#N)C>[Cl:26][C:27]1[CH:28]=[C:29]2[C:34](=[C:35]([Cl:37])[CH:36]=1)[CH2:33][N:32]([CH:38]1[CH2:40][CH2:39]1)[CH2:31][C@H:30]2[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[N:47]1[C:12](=[O:14])[CH2:11][C@H:3]([OH:4])[C:2]1=[O:6]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 66865035HCID 66865035, compoundHCID 66865129HCID 66865129, compound

Product 1

HCID 11626155HCID 11626155, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Analogously to example 49, ((R)-5-oxo-2-trichloromethyl[1,3]dioxolan-4-yl)acetic acid (94 mg, see Synthesis 2002, 2165), thionyl chloride (2 ml) and 2-((R)-6,8-dichloro-2-cyclopropyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylamine trifluoroacetic acid salt (200 mg) were reacted. The freeze-drying from water/acetonitrile afforded 31 mg of the desired product.

Sources & evidence

ORD record
ord-f413bedbe0a9425497babea6d2b0b802
Source dataset
uspto-grants-2011_01
Patent number
US07868003B2

Reaction notes

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