Triethylamine → HCID 11371942, compound

HRID 1356393Notes

Reaction equation

HRID 1356393 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@@H:13]([OH:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16](N(CC)CC)C.[C:23]1(C)[C:24]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:26]=[CH:27][CH:28]=1.C(OCC)(=O)C.CCCCCC>C(Cl)Cl>[S:29]([O:15][C@@H:13]([CH3:14])[CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])([C:24]1[CH:23]=[CH:28][C:27]([CH3:16])=[CH:26][CH:25]=1)(=[O:30])=[O:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 21226206Ethyl acetate hexaneHCID 54272252HCID 54272252, compound

Product 1

HCID 11371942HCID 11371942, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the product of Example-3A, (S)-1-[(benzyloxycarbonyl)amino]-2-propanol, (9.74 g, 46.7 mmol) and triethylamine 7.27 g, 72 mmol) in methylene chloride (60 mL) at 0° C. was added toluene sulfonyl chloride (9.15 g, 48 mmol) in methylene chloride (18 mL) slowly, in portions, over a period of 20 min while vigorously stirring under nitrogen. The mixture allowed to warm to room temperature and stirred for a further 36 hours under nitrogen. The organic layer was washed with 1N HCl, water, 5% NaHCO3 solution, water and brine before it was dried over anhydrous MgSO4. Evaporation of all solvent gave a white solid which was passed though a silica plug with ethyl acetate/hexane (1:4) to remove excess toluene sulfonyl chloride and then with ethyl acetate/hexane (1:3) to give the title product as white crystals. This material was recrystallized from ethyl acetate/hexane to give white needles (10.8 g). 1H NMR (CDCl3) δ 1.22 (d, 3H,) 2.39 (s, 3H), 3.20 (m, 1H), 3.43 (dd, 1H)), 4.66 (m, 1H), 5.02 (m, 1H), 5.04 (ABq, 2H), 7.34 (m, 7H), 7.77 (d, 2H). MS m/z (electrospray) 386 [M+23]+ (100%), 320 (66). The product was examined on a Regis Technologies Inc. Perkle Covalent (R,R) β-GEM1 HPLC column using mobile phase of isopropanol/hexane and a gradient of 10% isopropanol for 5 min, then 10 to 40% isopropanol over a period of 25 min, and using both UV and Laser Polarimetry detectors. Retention time major peak: 22.2 min, >98% ee.

Workup

  1. stirringstirred for a further 36 hours under nitrogen
  2. washThe organic layer was washed with 1N HCl, water, 5% NaHCO3 solution, water and brine before it
  3. dry with materialwas dried over anhydrous MgSO4
  4. customEvaporation of all solvent
  5. customgave a white solid which
  6. customto remove excess toluene sulfonyl chloride

Sources & evidence

ORD record
ord-5c3d152ce2fc4b21ba7c9080f6995069
Source dataset
uspto-grants-2003_07
Patent number
US06586474B2

Reaction notes

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