Carbon tetrabromide → HCID 131720252, compound

HRID 1489463Notes

Reaction equation

HRID 1489463 reaction equation
[CH2:1]([O:8][CH2:9][C@@:10]1([N:38]2[CH:46]=[C:44]([CH3:45])[C:42](=[O:43])[NH:41][C:39]2=[O:40])[O:33][C@H:13]([CH2:14][O:15][Si:16]([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:12]([CH2:34][CH2:35][CH2:36]O)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N-:66]=[N+:67]=[N-:68].[Li+].C(Br)(Br)(Br)Br>CN(C=O)C.CO>[CH2:1]([O:8][CH2:9][C@@:10]1([N:38]2[CH:46]=[C:44]([CH3:45])[C:42](=[O:43])[NH:41][C:39]2=[O:40])[O:33][C@H:13]([CH2:14][O:15][Si:16]([C:29]([CH3:32])([CH3:30])[CH3:31])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C@@H:12]([CH2:34][CH2:35][CH2:36][N:66]=[N+:67]=[N-:68])[CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 88163Lithium azideHCID 131720251HCID 131720251, compound

Product 1

HCID 131720252HCID 131720252, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Utilizing the conditions of Hetz et. al., J.C.S. Perkin 1 1980, 306, to a solution of compound 39 (1 eq) in DMF is added triphenylphosphine (1 eq) and lithium azide (5 eq) at room temperature. Carbon tetrabromide (1 eq) is added and the reaction mixture is stirred until judged complete by tlc. MeOH is added to quench the reaction mixture and the solvent is evaporated under reduced pressure. The residue is purified by silica gel chromatography to yield the title compound, 40.

Workup

  1. customto quench the reaction mixture
  2. customthe solvent is evaporated under reduced pressure
  3. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-6b60c150e2804933905f14d48a836d6c
Source dataset
uspto-grants-1997_10
Patent number
US05677437

Reaction notes

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