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

HRID 990087Notes

Reaction equation

HRID 990087 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([CH2:10][S:11][C:12]2[CH:20]=[CH:19][C:15]([CH2:16][CH2:17][NH2:18])=[CH:14][CH:13]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]([Si:25]([O:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH2:46][C@@H:47]2[CH2:49][O:48]2)=[CH:41][CH:40]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:24])([CH3:23])[CH3:22]>>[Si:25]([O:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH2:46][C@@H:47]([OH:48])[CH2:49][NH:18][CH2:17][CH2:16][C:15]2[CH:14]=[CH:13][C:12]([S:11][CH2:10][C:7]3[N:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[O:9][N:8]=3)=[CH:20][CH:19]=2)=[CH:41][CH:40]=1)([C:21]([CH3:22])([CH3:24])[CH3:23])([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 11327180t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilaneHCID 233890864-({[5-(Tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfanyl)phenethylamine

Product 1

HCID 59886865(2S)-1-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-3-{[4-({[5-(tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfanyl)phenethyl]amino}-2-propanolYield 12.9%

Procedure

Following the procedure described in Example 14 using the amine of Example 30 (0.481 g, 1.565 mmol) and tert-butyl{4-[(2S)oxiranylmethoxy]phenoxy}diphenylsilane (0.697 g, 1.721 mmol) afforded 0.140 g of the title compound.

Sources & evidence

ORD record
ord-5e39904143764b038ff86f5dcf737e2c
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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