O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → 1-[4-amino-3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-phenylalanyl)-4-(4-pyrimidinyl)piperazine

HRID 1782737Notes

Reaction equation

HRID 1782737 reaction equation
[NH2:1][C:2]1[C:20]([Br:21])=[CH:19][C:5]([CH2:6][C@H:7]([C:16]([OH:18])=O)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[Br:22].[N:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[N:25][CH:24]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>>[NH2:1][C:2]1[C:3]([Br:22])=[CH:4][C:5]([CH2:6][C@H:7]([C:16]([N:32]2[CH2:33][CH2:34][N:29]([C:26]3[CH:27]=[CH:28][N:23]=[CH:24][N:25]=3)[CH2:30][CH2:31]2)=[O:18])[NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[CH:19][C:20]=1[Br:21]

Participants

4

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 183211374-(Piperazin-1-yl)pyrimidineHCID 210234994-amino-3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-phenylalanine

Product 1

HCID 688559151-[4-amino-3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-phenylalanyl)-4-(4-pyrimidinyl)piperazineYield 92%

Procedure

Prepared analogously to Example A15a) from 4-amino-3,5-dibromo-N-(1,1-dimethylethoxycarbonyl)-D-phenylalanine and 1-(4-pyrimidinyl)piperazine in the presence of TBTU in a yield of 92% of theory. Colourless, amorphous substance, Rf=0.42 (FM4; Macherey-Nagel POLYGRAM® SIL G/UV254, ready-made films for TLC).

Sources & evidence

ORD record
ord-fc0ea97ec14f4862b0691b9ddf7c80bc
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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