L-Pyroglutamic Acid → HCID 131729168, compound

HRID 907448Notes

Reaction equation

HRID 907448 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][C@H:26]([C:52]([O:54]C)=[O:53])[CH2:27][C:28]1[N:32]=[CH:31][N:30]([C:33]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:29]=1.Cl.[NH:57]1[C:61](=[O:62])[CH2:60][CH2:59][C@H:58]1[C:63](O)=[O:64].CCN(C(C)C)C(C)C>CN(C=O)C>[NH:57]1[C:61](=[O:62])[CH2:60][CH2:59][C@H:58]1[C:63]([NH:25][C@H:26]([C:52]([OH:54])=[O:53])[CH2:27][C:28]1[N:32]=[CH:31][N:30]([C:33]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:29]=1)=[O:64]

Participants

6

Reactant 4

HCID 7405L-Pyroglutamic AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 53229896Methyl 1-(triphenylmethyl)-L-histidinate--hydrogen chloride (1/1)

Product 1

HCID 131729168HCID 131729168, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the general procedure for HBTU promoted coupling, 4.7 g (10.5 mmol) H-His(Trt)-OMe.HCl, 4.54 g (10.8 mmol) HBTU, 2.69 g (10.5 mmol) Pyr-OH and 8.3 ml (26.3 mmol) DIPEA were reacted in a CYTOS® Lab System in anhydrous DMF at total flow of 26.7 ml/min and a residence time of 1.2 min to yield 5.3 g of crude Pyr-His(Trt)-OH which was used in the next step without purification. Yield based on HPLC: 81%.

Sources & evidence

ORD record
ord-6bccb9e9fbed40029dfe614324bbd907
Source dataset
uspto-grants-2011_09
Patent number
US08013117B2

Reaction notes

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