Carbon tetrabromide → HCID 69349527, compound

HRID 1374414Notes

Reaction equation

HRID 1374414 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:22]O)[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:22][Br:25])[CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 15043091HCID 15043091, compound

Product 1

HCID 69349527HCID 69349527, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl(4S)-4-{[(benzyloxy)carbonyl]amino}-5-hydroxypentanoate (5.0 g, 15.5 mmol) in dichloromethane (50 ml) was cooled to 0° C. and carbontetrabromide (6.15 g, 18.5 mmol) was added thereto. At the same temperature triphenylphosphine (5.68 g, 21.7 mmol) was divided to five portions and they were added to the reaction mixture for every 2 minutes and the mixture was stirred for 30 minutes. The solvent was removed in vacuo. To the residue was added diethyl ether and mixture was stirred. After removal of the resulting crystall by filtration, the filtrate was condensed in vacuo and the residue was purified with silica gel chromatography to give tert-butyl(4S)-4-{[(benzyloxy)carbonyl]amino}-5-bromopentanoate (4.5 g, 80%).

Workup

  1. additionwere added to the reaction mixture for every 2 minutes
  2. customThe solvent was removed in vacuo
  3. additionTo the residue was added diethyl ether and mixture
  4. stirringwas stirred
  5. customAfter removal of the resulting crystall
  6. filtrationby filtration
  7. customcondensed in vacuo
  8. customthe residue was purified with silica gel chromatography

Sources & evidence

ORD record
ord-db5727b0025f48bdb50a07286d9c3401
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Reaction notes

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