Sodium hydride → 2-[N-Boc(amino)]-4-diethylphosphonomethylthiocarbonylthiazole

HRID 354032Notes

Reaction equation

[C:1]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[S:16])O)[N:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].O([CH2:27][P:28]([O:33][CH2:34][CH3:35])([O:30][CH2:31][CH3:32])=[O:29])S(C(F)(F)F)(=O)=O>C1COCC1>[C:1]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([CH2:27][P:28]([O:33][CH2:34][CH3:35])([O:30][CH2:31][CH3:32])=[O:29])=[S:16])[N:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of give 2-[N-Boc(amino)]-4-thiazolethiocarboxylic acid (1 mmole) in THF (5 mL) was cooled to −78° C. and treated with NaH (2 mmole) in small portions. After 10 min the reaction was treated with a solution of diethylphosphonomethyl triflate in THF (5 mL). The reaction was stirred at −78° C. for 1 h, and then quenched with H2O. Extraction and chromatography gave 2-[N-Boc(amino)]-4-diethylphosphonomethylthiocarbonylthiazole as a thick oil, which was subjected to Step D of Example 18 followed by Step C of Example 3 to give 2-amino-4-phosphonomethylthiocarbonylthiazole (18.5) as a solid. Mp>230° C. (decomp). Anal. Calcd. for C5H7N2O4PS2: C: 23.62; H: 2.78; N: 11.02. Found: C: 23.77; H: 2.61; N: 10.73.

Workup

customquenched with H2O
extractionExtraction and chromatography

Sources & evidence

ORD record: ord-51029354fede4434a86ee6430ffe76c5
Source dataset: uspto-grants-2004_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06756360B1

Reaction notes

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