Diisopropylethylamine → HCID 20298489, compound

HRID 1389217Notes

Reaction equation

HRID 1389217 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(N(C(C)C)C(C)C)C.[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([O:41][CH3:42])=[C:36]([CH:40]=1)[C:37](Cl)=[O:38]>C1C=CC=CC=1>[Cl:31][C:32]1[CH:33]=[CH:34][C:35]([O:41][CH3:42])=[C:36]([CH:40]=1)[C:37]([N:7]([CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:38]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 20298419HCID 20298419, compound

Product 1

HCID 20298489HCID 20298489, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Analogously to Example 47, 10.0 g of ethyl 4-(biphenyl-2-yl)aminobutyrate and 4.6 g of ethyldiisopropylamine in 50 ml of benzene are reacted with a solution of 7.3 g of 5-chloro-2-methoxybenzoyl chloride in 20 ml of benzene to obtain, as reaction product, 15.0 g (94.1% of theory) of ethyl 4-[5-chloro-2-methoxy-N-(biphenyl-2-yl)benzamido]butyrate as a viscous non-distillable oil. The saponification of this ester yields 12.4 g (88% of theory) of 4-[5-chloro-2-methoxy-N-(biphenyl-2-yl)benzamido-9 butyric acid, MP 160° to 162°.

Sources & evidence

ORD record
ord-e0d904b18133406ba5465ead1865169d
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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