Tert-butyl(4-chloro-but-2-ynyloxy)-dimethylsilane → methyl (S)-3-{4-[4-(tert-butyldimethylsilanyloxy)but-2-ynyloxy]benzoyl-amino}-2-(4-methanesulphonylpiperazin-1-yl)propanoate

HRID 517513Notes

Reaction equation

HRID 517513 reaction equation
[OH:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][CH2:9][C@H:10]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][CH2:16]2)[C:11]([O:13][CH3:14])=[O:12])=[O:7])=[CH:4][CH:3]=1.[C:27]([Si:31]([O:34][CH2:35][C:36]#[C:37][CH2:38]Cl)([CH3:33])[CH3:32])([CH3:30])([CH3:29])[CH3:28]>>[Si:31]([O:34][CH2:35][C:36]#[C:37][CH2:38][O:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][CH2:9][C@H:10]([N:15]2[CH2:16][CH2:17][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:19][CH2:20]2)[C:11]([O:13][CH3:14])=[O:12])=[O:7])=[CH:4][CH:3]=1)([C:27]([CH3:28])([CH3:29])[CH3:30])([CH3:32])[CH3:33]

Participants

3

Reactant 2

HCID 13403316Tert-butyl(4-chloro-but-2-ynyloxy)-dimethylsilaneHCID 67056914methyl (S)-3-(4-hydroxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoate

Product 1

HCID 86667910methyl (S)-3-{4-[4-(tert-butyldimethylsilanyloxy)but-2-ynyloxy]benzoyl-amino}-2-(4-methanesulphonylpiperazin-1-yl)propanoateYield 89.8%

Procedure

In a manner similar to example 4-5, starting from 400 mg (1 mmol) of methyl (S)-3-(4-hydroxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoate (prepared as described in example 4-4) and from 270 mg (1.2 mmol) of tert-butyl(4-chloro-but-2-ynyloxy)-dimethylsilane; 510 mg (88%) of methyl (S)-3-{4-[4-(tert-butyldimethylsilanyloxy)but-2-ynyloxy]benzoyl-amino}-2-(4-methanesulphonylpiperazin-1-yl)propanoate are obtained in the form of a colourless oil.

Sources & evidence

ORD record
ord-d30af802f3ff49ddb1798a0ed7bd41f8
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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