Trimethylsilyldiazomethane → HCID 75445982, compound

HRID 879704Notes

Reaction equation

HRID 879704 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-5a5b606ced7b425ea07c158f5cec6b64
Source dataset
uspto-grants-2015_03
Patent number
US08987295B2

Reaction notes

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