Triethylamine → 4-Butoxy-benzenesulfonic acid 4-(3-{[1-(4-butoxybenzene-sulfonyl)azetidin-3-yl]-tert-butoxycarbonyl-amino}-2-hydroxy-propoxy)-phenylester

HRID 2300210Notes

Reaction equation

HRID 2300210 reaction equation
C(OC(=O)N(C1CNC1)C[C@H](O)COC1C=CC(O)=CC=1)(C)(C)C.C(N(CC)CC)C.[CH2:32]([O:36][C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1)[CH2:33][CH2:34][CH3:35].[C:47]([O:51][C:52](=[O:84])[N:53]([CH:66]1[CH2:69][N:68]([S:70]([C:73]2[CH:78]=[CH:77][C:76]([O:79][CH2:80][CH2:81][CH2:82][CH3:83])=[CH:75][CH:74]=2)(=[O:72])=[O:71])[CH2:67]1)[CH2:54][C@H:55]([OH:65])[CH2:56][O:57][C:58]1[CH:63]=[CH:62][C:61]([OH:64])=[CH:60][CH:59]=1)([CH3:50])([CH3:49])[CH3:48].C(OC1C=CC(S(O)(=O)=O)=CC=1)CCC>C(Cl)(Cl)Cl>[CH2:80]([O:79][C:76]1[CH:77]=[CH:78][C:73]([S:70]([N:68]2[CH2:69][CH:66]([N:53]([C:52]([O:51][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:84])[CH2:54][CH:55]([OH:65])[CH2:56][O:57][C:58]3[CH:59]=[CH:60][C:61]([O:64][S:43]([C:40]4[CH:39]=[CH:38][C:37]([O:36][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:42][CH:41]=4)(=[O:45])=[O:44])=[CH:62][CH:63]=3)[CH2:67]2)(=[O:72])=[O:71])=[CH:74][CH:75]=1)[CH2:81][CH2:82][CH3:83]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 5179904-Butoxybenzenesulfonyl ChlorideHCID 12044733Azetidin-3-yl-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propyl]-carbamicacid tert-butyl esterHCID 12114477[1-(4-Butoxy-benzenesulfonyl)-azetidin-3-yl]-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propyl]-carbamic acid tert-butyl esterHCID 187677754-Butoxy-benzenesulfonic acid

Product 1

HCID 121144784-Butoxy-benzenesulfonic acid 4-(3-{[1-(4-butoxybenzene-sulfonyl)azetidin-3-yl]-tert-butoxycarbonyl-amino}-2-hydroxy-propoxy)-phenylester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of Azetidin-3-yl-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propyl]-carbamicacid tert-butyl ester (0.28 g, 0.8 mmol) in chloroform (4 ml) was added triethylamine (0.2 g, 2 mmol), and 4-butoxybenzenesulfonyl chloride (0.26 g, 1.0 mmol). The mixture was stirred at reflux for 5 h, and then quenched with 50% sodium bicarbonate solution. The chloroform was evaporated and the aqueous solution was removed. The residue was chromatographed (silica gel, ethyl acetate-hexanes/2:1) to give: (1) 0.13 g of [1-(4-Butoxy-benzenesulfonyl)-azetidin-3-yl]-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propyl]-carbamic acid tert-butyl ester as a colorless foam; MS (ES) m/z 551.1 (MH+); HRMS (El) Calcd. for C27H38N2O8S (M+): 550.2349, Found: 550.2353, and (2) 0.17 g of 4-Butoxy-benzenesulfonic acid 4-(3-{[(1-(4-butoxy-benzenesulfonyl)-azetidin-3-yl]-tert-butoxycarbonyl-amino}-2-hydroxy-propoxy)-phenylester as a colorless foam; MS (ES) m/z 763.3 (MH+); HRMS (ES) Calcd. for C37H51N2O11S2 (MH+): 763.2934, Found: 763.2899.

Workup

  1. temperatureat reflux for 5 h
  2. customquenched with 50% sodium bicarbonate solution
  3. customThe chloroform was evaporated
  4. customthe aqueous solution was removed
  5. customThe residue was chromatographed (silica gel, ethyl acetate-hexanes/2:1)
  6. customto give

Sources & evidence

ORD record
ord-1418feaff2dc457eb179f11e950fa8d7
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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