Methyl bromoacetate → HCID 131725938, compound

HRID 902946Notes

Reaction equation

HRID 902946 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][CH:8]([NH2:30])[C:9]([NH:11][CH:12]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH3:32]CN(C(C)C)C(C)C.BrC[C:43]([O:45][CH3:46])=[O:44]>C1COCC1>[C:1]([O:5][C:6](=[O:31])[CH2:7][CH:8]([N:30]([C:43]([O:45][CH3:46])=[O:44])[CH3:32])[C:9]([NH:11][CH:12]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 69213395HCID 69213395, compound

Product 1

HCID 131725938HCID 131725938, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of the dipeptide of Example 57 (100 mg, 0.23 mmol) in dry THF (2 mL) was added DIPEA (40 μL, 0.46 mmol). After the mixture became a homogenous solution, it was cooled to 0° C. and methyl bromoacetate (22 μL, 0.23 mmol) was introduced as a solution in dry THF (0.5 mL). The light suspension, which appeared shortly after, was stirred at 0° C. for 10 min and then at room temperature for 5 hours. The mixture was then concentrated in vacuum, dissolved in ethyl acetate and washed with H2O and brine. Drying (Na2SO4) and evaporation gave the title compound (92 mg) as a yellow foam. Flash chromatography (CH2Cl2 to 5% methanol in CH2Cl2) gave the desired product in 62% yield: 1HNMR (CDCl3, 300 MHz) □ 8.52 (br s, 1H), 7.82 (d, 1H), 7.59 (d, 1H), 7.38-7.02 (m, 4H), 4.75 (m, 1H), 4.18 (m, 1H), 3.68 (s, 3H), 3.61-3.21 (m and dd, 3H), 3.14 (dd, 1H), 2.85 (m, 2H), 1.42 (s, 9H), 1.36 (s, 9H); MS (Pos. FAB) 504.5 (MH)+.

Workup

  1. waitat room temperature for 5 hours
  2. concentrationThe mixture was then concentrated in vacuum
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with H2O and brine
  5. customDrying
  6. custom(Na2SO4) and evaporation

Sources & evidence

ORD record
ord-71ec5dd5e2034ebbb7b830e54e5e5bad
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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