Hydrochloric Acid → 2-[2-(-(S)-4-Amino-4-benzyloxycarbonylbutanamido)ethoxymethyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

HRID 1382623Notes

Reaction equation

HRID 1382623 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[CH2:29]([O:36][C:37]([C@@H:39]([NH:45]C(OC(C)(C)C)=O)[CH2:40][CH2:41][C:42](O)=[O:43])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.Cl>ClCCl.C(N(CC)CC)C>[NH2:45][C@H:39]([C:37]([O:36][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:38])[CH2:40][CH2:41][C:42]([NH:28][CH2:27][CH2:26][O:25][CH2:24][C:7]1[NH:8][C:9]([CH3:23])=[C:10]([C:19]([O:21][CH3:22])=[O:20])[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])[C:6]=1[C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:43]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 2162AmlodipineHCID 757711-HydroxybenzotriazoleHCID 1537081-(Phenylmethyl) hydrogen N-((1,1-dimethylethoxy)carbonyl)-L-glutamateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 228414582-[2-(-(S)-4-Amino-4-benzyloxycarbonylbutanamido)ethoxymethyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridineYield 17.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

The title compound (0.29 g) was prepared as an oil by the reaction of amlodipine (1.1 g), (S)-4-benzyloxycarbonyl-4-t-butoxycarbonylaminobutanoic acid (1.0 g) (commercially available), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.57 g), 1-hydroxybenzotriazole (0.40 g) and triethylamine (0.30 g) according to method of part (a) of Example 5 followed by treatment of the resulting intermediate in dichloromethane with gaseous hydrogen chloride according to the method of part (b).

Sources & evidence

ORD record
ord-26206dbdde964f3ebb4d25f5d52311b7
Source dataset
uspto-grants-1989_02
Patent number
US04806557

Reaction notes

Loading…