Pyridine → (s)-3-(2-Benzyloxybenzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester

HRID 1814371Notes

Reaction equation

HRID 1814371 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15](Cl)(=[O:17])=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][C:24](=[O:35])[CH2:25][C@H:26]([NH2:34])[CH:27]([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])([CH3:22])([CH3:21])[CH3:20].N1C=CC=CC=1>C(Cl)(Cl)Cl.C(OCC)(=O)C>[C:19]([O:23][C:24](=[O:35])[CH2:25][C@H:26]([NH:34][S:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:17])=[O:16])[CH:27]([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])([CH3:21])([CH3:20])[CH3:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 219624592-(Benzyloxy)benzene-1-sulfonyl chlorideHCID 86588238(S)-3-amino-4,4-diethoxy-butyric acid tert-butyl ester

Product 1

HCID 69692460(s)-3-(2-Benzyloxybenzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl esterYield 91.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Benzyloxy-benzenesulfonyl chloride (see Example 23, step 1) (1.7 g, 6 mmol) and (S)-3-amino-4,4-diethoxy-butyric acid tert-butyl ester (see Example 93) (1.5 g, 6 mmol) and pyridine (1.9 g, 30 mmol) were dissolved in chloroform (150 mL) and stirred at room temperature for 3 days. The reaction was diluted with ethyl acetate (500 mL) and washed with 5% citric acid, sat. sodium bicarbonate, and sat. sodium chloride. The organic layer was then dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash chromatography (SiO2, hexane:ethyl acetate, 8:1, then 4:1) gave the desired product (2.7 g, 91%) as a colorless oil. 1H NMR (400 MHz) CDCl3 δ 7.92 (m, 1H), 7.52 (d, 2H), 7.47 (t, 1H), 7.40 (t, 2H), 7.34 (d, 1H), 7.04 (t, 2H), 5.61 (d, 1H), 5.23 (q, 2H), 4.30 (d, 1H), 3.77 (m, 1H), 3.47 (m, 2H), 3.36 (m, 1H), 3.15 (m, 1H), 2.45 (t, 2H), 1.37 (s, 9H), 1.02 (t, 3H), 0.92 (t, 3H).

Workup

  1. washwashed with 5% citric acid, sat. sodium bicarbonate, and sat. sodium chloride
  2. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash chromatography (SiO2, hexane

Sources & evidence

ORD record
ord-a28b643372c44d9d973b7da33e48efa8
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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