1-(Morpholine-4-carboxamido)cyclohexanecarboxylic acid → N-[(S)-1-amino-1,2-dioxo-3-heptyl]-1-[N-[(2-methyl-2-propyloxycarbonyl)piperadine-4-carbonyl]amino]cyclohexanecarboxamide

HRID 1953443Notes

Reaction equation

HRID 1953443 reaction equation
N1([C:7]([NH:9][C:10]2([C:16]([OH:18])=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)=[O:8])CCOCC1.[CH3:19][C:20]([O:23][C:24](C1(C(NC2(C(O)=O)CCCCC2)=O)CCNCC1)=[O:25])([CH3:22])[CH3:21].CC([NH:48][C:49](=[O:58])[CH:50]([OH:57])[C@@H:51]([NH2:56])[CH2:52][CH2:53][CH2:54][CH3:55])(C)C.N[C@@H:60]([CH2:66][CH2:67]CC)[CH:61](O)[C:62]([NH2:64])=O>>[NH2:48][C:49](=[O:58])[C:50](=[O:57])[C@@H:51]([NH:56][C:16]([C:10]1([NH:9][C:7]([CH:60]2[CH2:61][CH2:62][N:64]([C:24]([O:23][C:20]([CH3:22])([CH3:21])[CH3:19])=[O:25])[CH2:67][CH2:66]2)=[O:8])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:18])[CH2:52][CH2:53][CH2:54][CH3:55]

Participants

5

Reactant 4

HCID 115071371-(Morpholine-4-carboxamido)cyclohexanecarboxylic acidHCID 21971170HCID 21971170, compoundHCID 54092353(2RS, 3S)-3-amino-2-hydroxyheptanamideHCID 1317219851-[N-[4-(2-methy-2-propyloxycarbonyl)piperadine-4-carbonyl]amino]cyclohexanecarboxylic acid

Product 1

HCID 15490909N-[(S)-1-amino-1,2-dioxo-3-heptyl]-1-[N-[(2-methyl-2-propyloxycarbonyl)piperadine-4-carbonyl]amino]cyclohexanecarboxamideYield 63%

Procedure

The same reaction procedure as in Example 1 was repeated except that the 1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarboxylic acid used in Example 1 was replaced by 1.06 g of 1-[N-[4-(2-methy-2-propyloxycarbonyl)piperadine-4-carbonyl]amino]cyclohexanecarboxylic acid, and (2RS,3S)-N-(2-methyl-2-propyl)-3-amino-2-hydroxyheptanamide used in Example 1 was replaced by 0.43 g of (2RS, 3S)-3-amino-2-hydroxyheptanamide synthesized in Reference Example 16, whereby 0.92 g of N-[(S)-1-amino-1,2-dioxo-3-heptyl]-1-[N-[(2-methyl-2-propyloxycarbonyl)piperadine-4-carbonyl]amino]cyclohexanecarboxamide was obtained in a yield of 63%.

Workup

  1. customThe same reaction procedure as in Example 1
  2. customsynthesized in Reference Example 16

Sources & evidence

ORD record
ord-a6043d5aff40404894d1df3de8704acd
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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