t-Butyl bromide → HCID 54129514, compound

HRID 900627Notes

Reaction equation

HRID 900627 reaction equation
[N:1]1([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:9][C@H:7]([OH:8])[CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].C([O-])([O-])=O.[K+].[K+].Br[C:27]([CH3:30])([CH3:29])[CH3:28]>CC(N(C)C)=O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[C:27]([O:4][C:3]([CH:2]1[CH2:6][CH:7]([OH:8])[CH2:9][N:1]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:5])([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 3

HCID 10485t-Butyl bromideHCID 11430Potassium CarbonateHCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Product 1

HCID 54129514HCID 54129514, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
55 °C

Procedure

A suspension of Cbz-Hyp-OH (4.854 g, 18 mmol) in DMA (135 ml), benzyltriethylammonium chloride (4.105 g, 18 mmol), K2CO3 (64 g, 46 mmol) and 2-bromo-2-methylpropane (99 ml, 859 mmol) was stirred at 55° C. for 18 hours. The mixture was diluted with iced water and extracted with EtOAc (3×). The organic phase washed with water, 0.5N NaHSO4 solution and brine dried and the solvent in vacuo to yield the title compound as a yellow oil (5.368 g, 98% yield). 1H-NMR (500 MHz, CDCl3) δ 1.33 (s, 5H), 1.47 (s, 4H), 2.01-2.14 (m, 1H), 2.22-2.38 (m, 1H), 3.50-3.72 (m, 2H), 4.34-4.45 (m, 1H), 4.45-4.53 (m, 1H), 5.04-5.20 (m, 2H), 7.22-7.42 (m, 5H). Analytical HPLC 10.14 min. LC-MS (ES+) m/e=322.2 (MH+).

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe organic phase washed with water, 0.5N NaHSO4 solution and brine
  3. customdried

Sources & evidence

ORD record
ord-76736e3ee6074194a9936c2c85a51225
Source dataset
uspto-grants-2008_04
Patent number
US07358273B2

Reaction notes

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