Bromine → HCID 22280687, compound

HRID 970696Notes

Reaction equation

HRID 970696 reaction equation
[C:1]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14]([O:16][CH2:17][P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])=[O:15])[N:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:26]Br>C(Cl)Cl>[C:1]([NH:8][C:9]1[S:10][C:11]([Br:26])=[C:12]([C:14]([O:16][CH2:17][P:18]([O:23][CH2:24][CH3:25])([O:20][CH2:21][CH3:22])=[O:19])=[O:15])[N:13]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 22280427HCID 22280427, compound

Product 1

HCID 22280687HCID 22280687, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[N-Boc(amino)]-4-diethylphosphonomethoxycarbonylthiazole (1 mmole) in CH2Cl2 (5 mL) was treated with bromine (2 mmole) at room temperature for 4 h. Evaporation and extraction gave 2-[N-Boc(amino)]-5-bromo-4-diethylphosphonomethoxycarbonylthiazole as an orange oil which was subjected to Step D of Example 18 followed by Step C of Example 3 to give 2-amino-5-bromo-4-phosphonomethoxycarbonylthiazole (18.2) as a solid. Mp>230° C. (decomp). Anal. Calcd. for C5H6N2O5PSBr: C, 18.94; H, 1.91; N, 8.84. Found: C, 19.08; H, 1.76; N, 8.67.

Workup

  1. customEvaporation and extraction

Sources & evidence

ORD record
ord-94d9b644b5104b0a9d62c650d0fdaf55
Source dataset
uspto-grants-2007_12
Patent number
US07312219B2

Reaction notes

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