5-Bromo-2-(triisopropylsilyl)thiazole → (S)-methyl 2-(tert-butoxycarbonyl)-3-(2-(triisopropylsilyl)thiazol-5-yl)propanoate

HRID 20031

Reaction equation

HRID 20031 reaction equation
[C:1]([O:5][C:6]([C@H:8]([CH2:13]I)[C:9]([O:11][CH3:12])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:16]1[S:20][C:19]([Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])=[N:18][CH:17]=1>>[C:1]([O:5][C:6]([C@@H:8]([CH2:13][C:16]1[S:20][C:19]([Si:21]([CH:25]([CH3:27])[CH3:26])([CH:28]([CH3:30])[CH3:29])[CH:22]([CH3:23])[CH3:24])=[N:18][CH:17]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 596011315-Bromo-2-(triisopropylsilyl)thiazoleHCID 86614124(R)-methyl2-(tert-butoxycarbonyl)-3-iodopropanoate

Product 1

HCID 67270410(S)-methyl 2-(tert-butoxycarbonyl)-3-(2-(triisopropylsilyl)thiazol-5-yl)propanoate

Procedure

The title compound was synthesized in a manner analogous to that described Example 475, using (R)-methyl 2-(tert-butoxycarbonyl)-3-iodopropanoate and 5-bromo-2-(triisopropylsilyl)thiazole (prepared according to Stangeland, Eric L.; Sammakia, Tarek, Use of Thiazoles in the Halogen Dance Reaction: Application to the Total Synthesis of WS75624 B, Journal of Organic Chemistry (2004), 69(7), 2381-2385.). MS m/z: 443.3 (100%, M+1).

Workup

  1. customprepared
  2. customApplication to the Total Synthesis of WS75624 B, Journal of Organic Chemistry (2004)

Sources & evidence

ORD record
ord-e39700be6b544b94bf846525f97b1aab
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Linked notes

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