t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilane → (2S)-1-{[4-({[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}-3-{4-[(triisopropylsilyl)oxy]phenoxy}-2-propanol

HRID 990085Notes

Reaction equation

HRID 990085 reaction equation
[C:1]([Si:5]([O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][C@@H:27]2[CH2:29][O:28]2)=[CH:21][CH:20]=1)([C:12]1[CH:17]=CC=C[CH:13]=1)[C:6]1[CH:11]=CC=C[CH:7]=1)(C)([CH3:3])[CH3:2].[CH3:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[O:42][N:41]=[C:40]([CH2:43][S:44]([C:47]3[CH:55]=[CH:54][C:50]([CH2:51][CH2:52][NH2:53])=[CH:49][CH:48]=3)(=[O:46])=[O:45])[N:39]=2)=[CH:34][CH:33]=1>>[CH3:30][O:31][C:32]1[CH:33]=[CH:34][C:35]([C:38]2[O:42][N:41]=[C:40]([CH2:43][S:44]([C:47]3[CH:48]=[CH:49][C:50]([CH2:51][CH2:52][NH:53][CH2:29][C@H:27]([OH:28])[CH2:26][O:25][C:22]4[CH:23]=[CH:24][C:19]([O:18][Si:5]([CH:1]([CH3:3])[CH3:2])([CH:6]([CH3:11])[CH3:7])[CH:12]([CH3:13])[CH3:17])=[CH:20][CH:21]=4)=[CH:54][CH:55]=3)(=[O:45])=[O:46])[N:39]=2)=[CH:36][CH:37]=1

Participants

3

Reactant 2

HCID 11327180t-butyl-[4-(2S)-oxiranylmethoxy-phenoxy]-diphenylsilaneHCID 120442034-({[5-(4-Methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethylamine

Product 1

HCID 70137905(2S)-1-{[4-({[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}-3-{4-[(triisopropylsilyl)oxy]phenoxy}-2-propanolYield 72.9%

Procedure

This material was prepared as described in Example 11 from tert-butyl{4-[(2S)oxiranylmethoxy]phenoxy}diphenylsilane (0.45 g, 1.124 mmol) and 4-({[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethylamine (0.70 g, 1.875 mmol). This procedure afforded 0.570 g of the title compound as a white foam.

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-caec5c71a65c4e61884698ae401cf9a2
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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