Hydrochloric Acid → ethyl 5-(N-t-butoxycarbonyl-L-leucyl)-4,5,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-acetate

HRID 1386460Notes

Reaction equation

HRID 1386460 reaction equation
[N:1]1[N:2]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:3]=[C:4]2[C:9]=1[CH2:8][CH2:7][NH:6][CH2:5]2.CC1C=CC(S(O)(=O)=O)=CC=1.Cl.[C:28]([O:32][C:33]([NH:35][C@H:36]([C:41](O)=[O:42])[CH2:37][CH:38]([CH3:40])[CH3:39])=[O:34])([CH3:31])([CH3:30])[CH3:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>>[C:28]([O:32][C:33]([NH:35][C@H:36]([C:41]([N:6]1[CH2:7][CH2:8][C:9]2=[N:1][N:2]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:3]=[C:4]2[CH2:5]1)=[O:42])[CH2:37][CH:38]([CH3:39])[CH3:40])=[O:34])([CH3:30])([CH3:31])[CH3:29]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 17794678HCID 17794678, compound

Product 1

HCID 70247611ethyl 5-(N-t-butoxycarbonyl-L-leucyl)-4,5,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-acetate

Procedure

In the same manner as in Example I-(1-A) except for using 0.30 g (0.79 mmol) of ethyl 4,5,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-acetate.TsOH in place of ethyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-acetate.HCl, 0.18 g (0.79 mmol) of N-t-butoxycarbonyl-L-leucine in place of N-t-butoxycarbonyl-L-4-nirophenylalanine and 0.30 g (0.79 mmol) of TBTU in place of BOP, the reaction was carried out to obtain ethyl 5-(N-t-butoxycarbonyl-L-leucyl)-4,5,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-acetate as pale brownish solid without purification.

Sources & evidence

ORD record
ord-a0a640febca24889afc92baa1b87245a
Source dataset
uspto-grants-2001_07
Patent number
US06265418B1

Reaction notes

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