Lithium Hydroxide → HCID 66913187, compound

HRID 1058459Notes

Reaction equation

HRID 1058459 reaction equation
[OH-:1].[Li+].COC(=O)/C(/NC(=O)C1C=CC(C(NCC2C=CC=C(O)C=2)=O)=CC=1Br)=[CH:7]/[C:8]1[S:9][CH:10]=[CH:11][N:12]=1.[O:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1.CO>>[CH3:7][C:8]1[S:9][C:36]([CH:37]=[CH:38][C:39]([OH:35])=[O:1])=[C:11]([CH3:10])[N:12]=1

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 23560730HCID 23560730, compound

Product 1

HCID 66913187HCID 66913187, compound

Procedure

A solution of 1N lithium hydroxide (0.3 mL, 0.3 mmol) is added to a solution of (Z)-2-[[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(thiazol-2-yl)propenoic acid methyl ester (Example 332; 55.6 mg, 0.1 mmol) in tetrahydrofuran/methanol (2:1; 1 mL). After the solution is allowed to stir at room temperature for 16 h, the volatiles are evaporated in vacuo and the residue is purified by reverse phase HPLC (increasing percentages of acetonitrile in water containing 0.1% trifluoroacetic acid). The appropriate fractions are combined and evaporated to yield to give (Z)-2-[2,6-dimethyl-4-[5-[(1H-indol-4-yl)methylamino]tetrazol-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid.

Workup

  1. customthe volatiles are evaporated in vacuo
  2. customthe residue is purified by reverse phase HPLC (increasing percentages of acetonitrile in water containing 0.1% trifluoroacetic acid)
  3. customevaporated
  4. customto yield

Sources & evidence

ORD record
ord-6658d13d2ad64975acdec6bad7b3f30d
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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