t-Butyl bromide → HCID 56985616, compound

HRID 2414593Notes

Reaction equation

HRID 2414593 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C@H:16]([C:20]([S:23][CH2:24][CH2:25][CH2:26][OH:27])([CH3:22])[CH3:21])[C:17]([OH:19])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[C:28](Br)([CH3:31])([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:15][C@H:16]([C:20]([S:23][CH2:24][CH2:25][CH2:26][OH:27])([CH3:21])[CH3:22])[C:17]([O:19][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:18])(=[O:14])=[O:13])=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 3

HCID 10485t-Butyl bromideHCID 11430Potassium CarbonateHCID 57110839HCID 57110839, compound

Product 1

HCID 56985616HCID 56985616, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (2S)-2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-3-[(3-hydroxypropyl)sulfanyl]-3-methylbutanoic acid from Example 171, (1 g, 2.41 mmol) in dimethylacetamide (6 mL) was added t-butyl bromide (4.16 mL, 36.2 mmol), potassium carbonate (2.66 g, 19.28 mmol), and benzyltriethylammonium chloride (82 mg, 0.36 mmol) and the resulting mixture was heated at 55° C. for 15 h. The solvent was removed and the residue was partitioned with ethylacetate and water. The organic layer was separated, washed with brine and dried over anhydrous sodium sulfate. The solvent was removed to obtain 600 mg (56%) of tert-butyl (2S)-2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-3-[(3-hydroxypropyl)sulfanyl]-3-methylbutanoate; 1H NMR (300 MHz, CDCl3) δ 1.22 (s, 9H), 1.35 (s, 3H), 1.39 (s, 3H), 1.76 (m, 2H), 1.80 (m, 3H), 2.41 (m, 1H), 2.68 (m, 2H), 3.71 (m, 3H), 4.69 (m, 2H), 5.74 (d, 1H, J=9.9 Hz), 7.03 (d, 2H, J=7.2 Hz), 7.79 (d, 2H, J=7.2 Hz); HRMS(C22H33NO6S2)(M+Na); cald. 494.1641, found 494.1644.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned with ethylacetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-e643b1b19e9f4ea99740027278f60511
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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