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

HRID 1386459Notes

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:44](O)=[O:45])[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:34])([CH3:31])([CH3:30])[CH3:29].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>>[C:28]([O:32][C:33]([NH:35][C@H:36]([C:44]([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:45])[CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:34])([CH3:30])([CH3:31])[CH3:29]

Participants

Reactant 5

HCID 313Hydrochloric Acid

HCID 6101p-Toluenesulfonic acid

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 17794678HCID 17794678, compound

Product 1

HCID 70244420ethyl 5-(N-t-butoxycarbonyl-L-phenylalanyl)-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, 0.20 g (0.79 mmol) of N-t-butoxycarbonyl-L-phenylalanine in place of N-t-butoxycarbonyl-L-4-nirophenylalanine and 0.33 g (0.87 mmol) of HBTU in place of BOP, the reaction was carried out to obtain ethyl 5-(N-t-butoxycarbonyl-L-phenylalanyl)-4,5,6,7-tetrahydropyrazolo[4,3-c]pyridin-2-acetate as pale brownish solid without purification.

Sources & evidence

ORD record: ord-8ffbdc1fab924591b8cba80b465df76f
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265418B1

Reaction notes

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