Hydrochloric Acid → HCID 178454288, compound

HRID 1497491Notes

Reaction equation

HRID 1497491 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[N:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[NH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.O[C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][CH2:49][C:50]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[O:51])=[CH:43][CH:42]=1.Cl>ClCCl.CN(C1C=CN=CC=1)C>[C:24]([O:23][C:21]([NH:20][C:9](=[N:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[NH:10][C:11]1[CH:19]=[CH:18][C:14]([C:15]([O:17][C:41]2[CH:42]=[CH:43][C:44]([CH2:47][CH2:48][CH2:49][C:50]([O:52][CH2:53][C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[O:51])=[CH:45][CH:46]=2)=[O:16])=[CH:13][CH:12]=1)=[O:22])([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 89451939Benzyl 4-(4-hydroxyphenyl)butanoateHCID 178454296HCID 178454296, compound

Product 1

HCID 178454288HCID 178454288, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoic acid (2.96 g) in dichloromethane (20.0 mL) were added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.80 g), benzyl 4-(4-hydroxyphenyl)butanoate (2.00 g), and N,N-dimethyl-4-aminopyridine (286 mg), followed by stirring at room temperature overnight. To a reaction solution was added 1 M hydrochloric acid, followed by concentrating under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 4-[4-(benzyloxy)-4-oxobutyl]phenyl 4-[N′,N″-bis(tert-butoxycarbonyl)carbamimidamido]benzoate (3.98 g).

Workup

  1. concentrationby concentrating under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-327a4a21dd604a90bef6f0f302357b01
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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