L-Pyroglutamic Acid → HCID 58746683, compound

HRID 724645Notes

Reaction equation

HRID 724645 reaction equation
[O:1]=[C:2]1[NH:6][C@H:5]([C:7]([OH:9])=O)[CH2:4][CH2:3]1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.[NH2:43][C@@H:44]([CH2:64][C:65]1[CH:70]=[CH:69][C:68]([CH:71]2[S:75](=[O:77])(=[O:76])[NH:74][C:73](=[O:78])[CH2:72]2)=[CH:67][CH:66]=1)[C:45]([NH:47][CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]1[CH:62]=[CH:61][CH:60]=[C:59]([OH:63])[C:54]=1[C:55]([O:57][CH3:58])=[O:56])=[O:46]>CN(C=O)C>[O:76]=[S:75]1(=[O:77])[CH:71]([C:68]2[CH:67]=[CH:66][C:65]([CH2:64][C@H:44]([NH:43][C:7]([C@@H:5]3[CH2:4][CH2:3][C:2](=[O:1])[NH:6]3)=[O:9])[C:45]([NH:47][CH2:48][CH2:49][CH2:50][CH2:51][O:52][C:53]3[CH:62]=[CH:61][CH:60]=[C:59]([OH:63])[C:54]=3[C:55]([O:57][CH3:58])=[O:56])=[O:46])=[CH:70][CH:69]=2)[CH2:72][C:73](=[O:78])[NH:74]1

Participants

6

Reactant 4

HCID 7405L-Pyroglutamic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69597926HCID 69597926, compound

Product 1

HCID 58746683HCID 58746683, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S)-5-oxopyrrolidine-2-carboxylic acid (2.0 mg, 0.015 mmol) in DMF (0.5 mL) was added N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (5.8 mg, 0.015 mmol) and N,N-diisopropylethylamine (0.008 mL, 0.045 mmol) and premixed for 5 minutes. To the solution was added methyl 2-[4-({(2S)-2-amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoyl}amino)-butoxy]-6-hydroxybenzoate (8.0 mg, 0.015 mmol) and stirred overnight at room temperature. The product was purified by preparative LCMS to afford the desired product (1.4 mg). LCMS found for C29H35N4O10S (M+H)+: m/z=631.0

Workup

  1. additionpremixed for 5 minutes
  2. customThe product was purified by preparative LCMS

Sources & evidence

ORD record
ord-e00d916125d94010a833d9ad1a9cd36e
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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