Ammonia → HCID 21866542, compound

HRID 1582909Notes

Reaction equation

HRID 1582909 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([CH3:18])=[C:13]([C:15](O)=[O:16])[N:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([N:21](CC)CC)C.ClC(OCC(C)C)=O.N>C1COCC1>[C:1]([NH:8][CH2:9][C:10]1[S:11][C:12]([CH3:18])=[C:13]([C:15]([NH2:21])=[O:16])[N:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 21866470232280-96-5

Product 1

HCID 21866542HCID 21866542, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

2-(N-Boc-Aminomethyl)-5-methylthiazole-4-carboxylic acid (6.8 g, 25 mmol) was dissolved in THF (100 ml), and triethylamine (2.53 g, 25 mmol) was added. After the mixture had been cooled to −20° C., a solution of isobutyl chloroformate (3.41 g, 25 mmol) in THF (10 ml) was added dropwise. After the mixture had been stirred for 30 minutes at −20° C., ammonia gas was passed into the pale brown suspension for 45 minutes. The mixture was then warmed to room temperature. The residue was filtered off with suction and extracted with THF, and the filtrates were concentrated.

Workup

  1. temperatureThe mixture was then warmed to room temperature
  2. filtrationThe residue was filtered off with suction
  3. extractionextracted with THF
  4. concentrationthe filtrates were concentrated

Sources & evidence

ORD record
ord-ec5ce75b1f9b495f942b0995ee848ffd
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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