Water → HCID 69654940, compound

HRID 1794932Notes

Reaction equation

HRID 1794932 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]2[CH2:26][CH:25]([N:27]([CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH2:28][C@H:29]([OH:46])[CH2:30][O:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:34][CH:33]=3)[CH2:24]2)=[CH:19][CH:18]=1.C(N(CC)CC)C.O>C(Cl)Cl>[CH2:47]([N:27]([CH2:28][C@H:29]([OH:46])[CH2:30][O:31][C:32]1[CH:33]=[CH:34][C:35]([O:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[CH:36][CH:37]=1)[CH:25]1[CH2:24][N:23]([C:20]2[CH:19]=[CH:18][C:17]([NH:16][S:12]([C:9]3[CH:10]=[CH:11][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][CH:8]=3)(=[O:14])=[O:13])=[CH:22][CH:21]=2)[CH2:26]1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5179904-Butoxybenzenesulfonyl ChlorideHCID 69655043HCID 69655043, compound

Product 1

HCID 69654940HCID 69654940, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Butoxybenzenesulfonyl chloride (0.20 g, 0.79 mmol) was added to a solution of (2S)-1-{[1-(4-amino-phenyl)-azetidin-3-yl]-benzyl-amino}-3-(4-benzyloxy-phenoxy)-propan-2-ol (which was obtained in Example 401) (0.37 g, 0.727 mmol) and triethylamine (0.56 mL, 3.99 mmol) in anhydrous methylene chloride (7 mL). The reaction was stirred at room temperature overnight. The solution was then treated with water (30 mL) followed by extraction with ethyl acetate (3×30 mL). The organic extract was dried with anhydrous sodium sulfate, filtered and concentrated to afford a crude solid. The desired product was isolated using silica gel flash chromatography to give 90 mg of an off-white solid; 1H NMR (300 MHz, CDCl3) δ 0.99(t, 3H, J=5.04 Hz), 1.47(m, 2H), 1.78(m, 2H), 2.69(m, 2H), 3.08(brs, 1H), 3.65(m, 3H), 3.78(m, 2H), 3.87(m, 4H), 3.95(t, 2H, J=6.45 Hz), 5.01 (s, 2H), 6.01(s, 1H), 6.29(d, 2H, J=8.73 Hz), 6.86(m, 10H), 7.35(m, 8H), 7.56(d, 2H, J=8.94 Hz). MS (ES) m/z: 722.1 (MH+); Anal. Calcd. for C42H47N3O6S: C, 69.88; H, 6.56; N, 5.82. Found: C, 68.91; H, 6.38; N, 5.55.

Workup

  1. extractionfollowed by extraction with ethyl acetate (3×30 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a crude solid

Sources & evidence

ORD record
ord-f38ebc18e8cc40e5bb455a5cb35a75e2
Source dataset
uspto-grants-2006_04
Patent number
US07022716B2

Reaction notes

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