HCID 56986282, compound → (2RS,3S)-2-hydroxy-3-[N-[1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarbonyl]amino]heptanoic acid

HRID 1953440Notes

Reaction equation

HRID 1953440 reaction equation
[OH:1][CH:2]([C@@H:13]([NH:18][C:19]([C:21]1([NH:27][C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:20])[CH2:14][CH2:15][CH2:16][CH3:17])[C:3]([O:5]CC1C=CC=CC=1)=[O:4]>[C].[Pd].CO>[OH:1][CH:2]([C@@H:13]([NH:18][C:19]([C:21]1([NH:27][C:28]([N:30]2[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:20])[CH2:14][CH2:15][CH2:16][CH3:17])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 1

HCID 56986282HCID 56986282, compound

Product 1

HCID 11603694(2RS,3S)-2-hydroxy-3-[N-[1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarbonyl]amino]heptanoic acidYield 100.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Further, to methanol 100 ml solution of 16.8 g (34 mmol) of the above phenylmethyl (2RS,3S)-2-hydroxy-3-[N-[1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarbonyl]amino]heptanoate, 1.5 g of 10% palladium carbon was added under haydrogen atmosphere and was stirred at the room temperature for two hours. After insoluble components of the reaction solution were removed by filtration, the filtrate was concentrated under reduced pressure, whereby 13.6 g of the captioned (2RS,3S)-2-hydroxy-3-[N-[1-[N-(morpholine-4-carbonyl)amino]cyclohexanecarbonyl]amino]heptanoic acid was obtained in a yield of 68%.

Workup

  1. customAfter insoluble components of the reaction solution were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a4d15aab39f2487889323a730f873ff5
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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