t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilane → (2S)-1-[(4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethyl)amino]-3-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-2-propanol

HRID 990080Notes

Reaction equation

HRID 990080 reaction equation
[CH2:1]([C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14]([C:16]2[CH:24]=[CH:23][C:19]([CH2:20][CH2:21][NH2:22])=[CH:18][CH:17]=2)=[O:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([Si:29]([O:42][C:43]1[CH:48]=[CH:47][C:46]([O:49][CH2:50][C@@H:51]2[CH2:53][O:52]2)=[CH:45][CH:44]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([CH3:28])([CH3:27])[CH3:26].ClCCl.C(Cl)(Cl)Cl.CO>CO.C1COCC1>[CH2:1]([C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14]([C:16]2[CH:17]=[CH:18][C:19]([CH2:20][CH2:21][NH:22][CH2:53][C@H:51]([OH:52])[CH2:50][O:49][C:46]3[CH:45]=[CH:44][C:43]([O:42][Si:29]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:48][CH:47]=3)=[CH:23][CH:24]=2)=[O:15])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11327180t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilaneHCID 120442084-{[(5-Benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethylamineHCID 86584582Dichloromethane chloroform methanol

Product 1

HCID 12044209(2S)-1-[(4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethyl)amino]-3-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-2-propanolYield 41.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

A solution of the amine of Example 22 (0.705 g, 2.00 mmol) and the epoxide of Example 9 (0.640 g, 1.594 mmol) in a mixture of methanol (25 mL) and THF (5 mL) was heated to 45° C. for 23 h. TLC shows characteristic product spot at Rf=0.2 5(silica gel plate; dichloromethane/chloroform/methanol: 20/5/2). The reaction mixture was cooled, silica gel (5 g) was added and the methanol was remove in vacuo. The reaction mixture, preabsorbed onto silica gel was applied to the top of a flash chromatography column(silica gel; dichloromethane/chloroform/methanol: 12/3/1) and purified in the standard manner. This procedure afforded 0.490 g of the title compound as a white foam.

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionsilica gel (5 g) was added
  3. customthe methanol was remove in vacuo
  4. customThe reaction mixture, preabsorbed onto silica gel
  5. custompurified in the standard manner

Sources & evidence

ORD record
ord-34a2e239ea4845b3872260d08bfb8cc4
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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