tert-Butyl carbazate → HCID 87174988, compound

HRID 1947713Notes

Reaction equation

HRID 1947713 reaction equation
[CH3:1][Si:2]([CH3:14])([CH3:13])[C:3]#[C:4][C:5](=O)[CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10].[C:15]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[NH:16][NH2:17]>CC(O)C>[C:20]([O:19][C:15]([NH:16]/[N:17]=[C:5](\[C:4]#[C:3][Si:2]([CH3:14])([CH3:13])[CH3:1])/[CH2:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 15312642HCID 15312642, compound

Product 1

HCID 87174988HCID 87174988, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 54.0 g (254 mmol) of 7-(trimethylsilyl)-5-oxohept-6-ynoic acid from step A above in 750 mL of IPA under an atmosphere of nitrogen was added 33.6 g (254 mmol) of tert-butyl carbazate. The reaction mixture was stirred for 4 h at ambient temperature then evaporated in vacuo to remove all volatiles. This afforded the title compound as a yellow gum which was used without further purification (77 g, 93%). LC-MS: m/z (ES) 327 (MH)+.

Workup

  1. customthen evaporated in vacuo
  2. customto remove all volatiles

Sources & evidence

ORD record
ord-c3a32e18f2d94129baabc4ae22a06db3
Source dataset
uspto-grants-2013_03
Patent number
US08399480B2

Reaction notes

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