Trimethylsilyldiazomethane → HCID 75445982, compound

HRID 708595Notes

Reaction equation

HRID 708595 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:10][C:11]([C:15]([OH:17])=[O:16])=[C:12]([CH3:14])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si](C=[N+]=[N-])(C)(C)[CH3:19]>C1COCC1.CO>[CH3:19][O:16][C:15]([C:11]1[S:10][C:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[N:13][C:12]=1[CH3:14])=[O:17]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 2756770N-Boc-amino-4-methylthiazole-5-carboxylic acid

Product 1

HCID 75445982HCID 75445982, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-tert-Butoxycarbonylamino-4-methyl-thiazole-5-carboxylic acid (0.52 g) was dissolved in THF: MeOH (2:1, 10 mL) and 2 eq of TMSCHN2 (2M sln in hex) was added at RT and stirred for 6 h. All volatiles were removed in vacuum by rotavap and the residue was dried in vacuum to give 2-tert-Butoxycarbonylamino-4-methyl-thiazole-5-carboxylic acid methyl ester (0.52 g). This was used in the next reaction without further purification. 1H NMR (400 MHz, CDCl3) 3.83 (s, 3H), 2.65 (s, 3H), 1.54 (s, 9H).

Workup

  1. customAll volatiles were removed in vacuum by rotavap
  2. customthe residue was dried in vacuum

Sources & evidence

ORD record
ord-75ed62ea271949ba984a7fcd013b5e43
Source dataset
uspto-grants-2015_11
Patent number
US09175003B2

Reaction notes

Loading…