Water → HCID 69654940, compound

HRID 1061428Notes

Reaction equation

HRID 1061428 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=8.73Hz), 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-723ff17033cd40b9872dfc08bb828ff7
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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