Carbon Tetrachloride → HCID 58126861, compound

HRID 1971819Notes

Reaction equation

HRID 1971819 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:41])[CH2:10][NH:11][C:12]([C:14]2[N:15]=[C:16]3[N:31]([CH2:32][C:33](=[O:40])[N:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)[CH:30]=[CH:29][N:17]3[C:18](=[O:28])[C:19]=2[O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=O)=[CH:4][CH:3]=1.C(Cl)(Cl)(Cl)Cl.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[CH2:21]([O:20][C:19]1[C:18](=[O:28])[N:17]2[CH:29]=[CH:30][N:31]([CH2:32][C:33](=[O:40])[N:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)[C:16]2=[N:15][C:14]=1[C:12]1[O:41][C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:10][N:11]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 58126888HCID 58126888, compound

Product 1

HCID 58126861HCID 58126861, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the product of example 5 (200 mg, 0.357 mmol) in acetonitrile (3 ml), carbon tetrachloride (330 mg, 2.1 mmol), triethylamine (180 mg, 1.78 mmol) and triphenylphosphine (470 mg, 1.79 mmol) were added successively at room temperature. The mixture was stirred for 3 hours. The product was purified by column chromatography (CH2Cl2/MeOH=150/1) to give the titled product (40 mg, 21% yield).

Workup

  1. customThe product was purified by column chromatography (CH2Cl2/MeOH=150/1)

Sources & evidence

ORD record
ord-9105e04a8cff4cbe880b8848d8ce54d6
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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