Calcium hydride → Ureidovaline

HRID 1275359Notes

Reaction equation

HRID 1275359 reaction equation
[H-].[Ca+2].[H-].[CH3:4][NH:5][CH2:6][C:7]1[N:8]=[C:9]([CH:12]([CH3:14])[CH3:13])[S:10][CH:11]=1.[O:15]([C:22]([NH:24][C@H:25]([C:29]([OH:31])=[O:30])[CH:26]([CH3:28])[CH3:27])=O)C1C=CC=CC=1>C1COCC1>[CH3:4][N:5]([C:22]([NH:24][C@H:25]([C:29]([OH:31])=[O:30])[CH:26]([CH3:28])[CH3:27])=[O:15])[CH2:6][C:7]1[N:8]=[C:9]([CH:12]([CH3:14])[CH3:13])[S:10][CH:11]=1

Participants

5

Reactant 3

HCID 3033859Calcium hydrideHCID 9816135N-Phenoxycarbonyl-L-valineHCID 107496872-Isopropyl-4-(N-methyl)amino-methyl thiazole

Product 1

HCID 9818282Ureidovaline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
20 °C

Procedure

To a suspension of calcium hydride (o.98 g, 23.2 mmol) in THF (25 mL) at 0° C. to 5° C. was added 3.94 g (23.1 mmol) of N-methyl-N-((2-isopropyl-4-thiazolyl)methyl)amine. To this was added a solution of N-phenoxycarbonyl-L-Valine (5.0 g, 21.1 mmol) in 20 mL of THF. Following a 5 mL THF rinse, 4.0 mL of water was added, and the reaction mixture was allowed to warm to 20° C. with stirring. After 2 hours, HPLC analysis (t=12.6 min; HPLC conditions: 65% 0.03M KH2PO4 buffer/35% acetonitrile; pH=4; 5μ nucleosil; 4.6×250 mm; 1 mL/min; 205 nm) indicated that the reaction was complete and the desired product had been formed.

Workup

  1. washrinse
  2. addition4.0 mL of water was added
  3. customHPLC analysis (t=12.6 min; HPLC conditions: 65% 0.03M KH2PO4 buffer/35% acetonitrile; pH=4; 5μ nucleosil; 4.6×250 mm; 1 mL/min; 205 nm)

Sources & evidence

ORD record
ord-d943d8739e09425d92597104b049b182
Source dataset
uspto-grants-2000_12
Patent number
US06160122

Reaction notes

Loading…