2-Chloromethyl 2-(trimethylsilyl)ethyl ether → (S)-2-(7-bromo-5-methyl-2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydrobenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

HRID 1468715Notes

Reaction equation

HRID 1468715 reaction equation
[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:25]([CH3:26])=[CH:24][C:18]2[N:19]([CH3:23])[C:20](=[O:22])[S:21][C:17]=2[C:16]=1[Br:27])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C(OC[C@H](C1C(C)=CC2N=C(O)SC=2C=1Br)OC(C)(C)C)(=O)C(C)(C)C.[CH3:54][Si:55]([CH3:62])([CH3:61])[CH2:56][CH2:57][O:58]CCl>>[C:1]([O:7][CH2:8][C@H:9]([C:15]1[C:25]([CH3:26])=[CH:24][C:18]2[N:19]([CH2:23][O:58][CH2:57][CH2:56][Si:55]([CH3:62])([CH3:61])[CH3:54])[C:20](=[O:22])[S:21][C:17]=2[C:16]=1[Br:27])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:6])[C:2]([CH3:3])([CH3:5])[CH3:4]

Participants

4

Reactant 3

HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 70981530(S)-2-(7-bromo-3,5-dimethyl-2-oxo-2,3-dihydrobenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalateHCID 178422341HCID 178422341, compound

Product 1

HCID 70981261(S)-2-(7-bromo-5-methyl-2-oxo-3-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydrobenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate

Procedure

Prepared by the similar method to make (S)-2-(7-bromo-3,5-dimethyl-2-oxo-2,3-dihydrobenzo[d]thiazol-6-yl)-2-tert-butoxyethyl pivalate (67C) in example 26 from 67B using 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl) instead of methyl iodide.

Workup

  1. customPrepared by the similar method

Sources & evidence

ORD record
ord-cd70a248388745178d6c5debfa623897
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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