Benzyl Bromide → HCID 58017458, compound

HRID 1879229Notes

Reaction equation

HRID 1879229 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:9]([NH:12][C@@H:13]([C:18]([OH:20])=[O:19])[C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[CH2:27]([O:19][C:18](=[O:20])[C@@H:13]([C:14]([CH3:16])([CH3:17])[CH3:15])[NH:12][S:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:11])=[O:10])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58017457HCID 58017457, compound

Product 1

HCID 58017458HCID 58017458, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(3 Methoxyphenylsulfonyl)D-tert-leucine (3.03 g, 10.1 mmol) is dissolved in DMF (30 ml). Potassium Carbonate (2.81 g, 20.1 mmol) is added followed by Benzyl Bromide (1.21 ml, 9.95 mmol) and the reaction is stirred at ambient temperature for 18 hours. The reaction mixture is partitioned between Ethyl Acetate and 1 N HCl. The organics are separated and washed with brine, dried over MgSO4 and concentrated. The residue is purified by column chromatography eluting with a gradient of 5-60% (Hex-EtOAc) to give the title compound (3.08 g, 78% yield). Mass spectrum (392.2; M+1, 390.2; M−1).

Workup

  1. customThe reaction mixture is partitioned between Ethyl Acetate and 1 N HCl
  2. customThe organics are separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography
  7. washeluting with a gradient of 5-60% (Hex-EtOAc)

Sources & evidence

ORD record
ord-206582207ede4c51b5916f951b9767b6
Source dataset
uspto-grants-2012_11
Patent number
US08314148B2

Reaction notes

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