Benzyl Bromide → HCID 70004574, compound

HRID 1264398Notes

Reaction equation

HRID 1264398 reaction equation
[C:1]([O:5][C:6](=[O:49])[CH2:7][NH:8][C:9]([C@@H:11]1[CH2:15][C@@H:14]([S:16][C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][N:12]1[S:36]([C:39]1[CH:48]=[CH:47][C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=1)(=[O:38])=[O:37])=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH2:50](Br)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.[H-].[Na+].[NH4+].[Cl-].CCOC(C)=O>CN(C=O)C>[C:1]([O:5][C:6](=[O:49])[CH2:7][N:8]([CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:9]([C@@H:11]1[CH2:15][C@@H:14]([S:16][C:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:13][N:12]1[S:36]([C:39]1[CH:48]=[CH:47][C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=1)(=[O:38])=[O:37])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 70001149HCID 70001149, compoundHCID 86583716Ammonium chloride ethyl acetate

Product 1

HCID 70004574HCID 70004574, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 346.5 mg (0.5 mmol) (2S,4R)-{[1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carbonyl]-amino}-acetic acid tert-butyl ester in 3 ml DMF was treated at 0° C. with 0.24 ml (2 mmol) benzylbromide and 35 mg (0.8 mmol) 55% NaH, warmed up over night to RT. The reaction was poured into aqueous saturated NH4Cl/EtOAc (3×). The organic phase was washed with aqueous 10% NaCl solution, dried over Na2SO4 and evaporated under reduced pressure. Purification by flash-chromatography on silicagel (Hexane/EtOAc 9:1) gave 277 mg (71%) (2S,4R)-[Benzyl-[1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carbonyl]- amino}-acetic acid tert-butyl ester, MS: 781 (M-H)−.

Workup

  1. washThe organic phase was washed with aqueous 10% NaCl solution
  2. dry with materialdried over Na2SO4
  3. customevaporated under reduced pressure
  4. customPurification by flash-chromatography on silicagel (Hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-fed7bcfbd112481e98094fb25e692b14
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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