Trifluoroacetic acid methylene chloride → 3-benzyloxycarbonylamino-6-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid

HRID 10973

Reaction equation

HRID 10973 reaction equation
C([O:5][C:6]([C:8]1([CH3:29])[N:12]2[C:13](=[O:28])[C:14]([NH:17][C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[CH:15][N:16]=[C:11]2[CH2:10][CH2:9]1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl>O>[CH2:21]([O:20][C:18]([NH:17][C:14]1[C:13](=[O:28])[N:12]2[C:8]([CH3:29])([C:6]([OH:7])=[O:5])[CH2:9][CH2:10][C:11]2=[N:16][CH:15]=1)=[O:19])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 696008793-benzyloxycarbonylamino-6-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic Acid tert-butyl Ester

Product 1

HCID 219796983-benzyloxycarbonylamino-6-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic AcidYield 105.5%

Reagents, catalysts & solvents 1

HCID 962WaterCatalyst

Procedure

A solution of intermediate 19a (55 mg, 0.138 mmol) in 4 mL 1:1 TFA/CH2Cl2 with 2 drops water was stirred at rt for 12 h. The mixture was concentrated in vacuo, then coevaporated with CCl4 to afford 50 mg of intermediate 19b (quantitative), which was used without further purification in the following step.

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-87b4f71a3c464d95bdbbcf9b03be006a
Source dataset
uspto-grants-2006_08
Patent number
US07094783B2

Linked notes

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