Triethylamine → HCID 178501234, compound

HRID 413718Notes

Reaction equation

HRID 413718 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:5][CH2:4]1.[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22](O)=[O:23])[CH2:15][CH2:14]1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC>O.OC1C2N=NNC=2C=CC=1.ClCCl>[O:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][C:22]([NH:2][C@@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]([O:11][CH3:12])=[O:10])[CH2:7][CH2:8]2)=[O:23])[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 798724-Morpholinebutanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178501209HCID 178501209, compound

Product 1

HCID 178501234HCID 178501234, compoundYield 73.8%

Reagents, catalysts & solvents 2

HCID 178526939HCID 178526939, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

The procedure is carried out in a manner similar to that described in Example 63, but starting with 4.20 g of methyl cis-4-aminocyclohexane-1-carboxylate hydrochloride, 4.0 g of 4-morpholinobutyric acid, 50 mg of hydroxybenzotriazole hydrate, 11.2 cm3 of triethylamine, 200 cm3 of dichloromethane and 4.2 g of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride. After a treatment similar to that in Example 60, the crude product is purified by flash chromatography [eluent: dichloromethane/methanol (95/5 by volume)] to give 5.0 g of methyl cis-4-(4-morpholinobutyrylamino)-1-cyclohexanecarboxylate in the form of a yellow oil.

Workup

  1. customAfter a treatment similar to that in Example 60, the crude product is purified by flash chromatography [eluent: dichloromethane/methanol (95/5 by volume)]

Sources & evidence

ORD record
ord-ae1753f6db8d440aa460b80da9b16d44
Source dataset
uspto-grants-2003_05
Patent number
US06569854B1

Reaction notes

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