Isonicotinic Acid → HCID 12993582, compound

HRID 2179921Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:11]([OH:15])[C@H:10]([NH2:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:17]1[CH:22]=[CH:21][C:20]([C:23](O)=[O:24])=[CH:19][CH:18]=1.CN(C1C=CC=CN=1)C.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.O>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:11]([OH:15])[C@H:10]([NH:16][C:23]([C:20]2[CH:21]=[CH:22][N:17]=[CH:18][CH:19]=2)=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 5 °C

Procedure

36.85 g of (3R,4S)-3-Amino-4-hydroxy-azepane-1-carboxylic acid tert-butyl ester, 19.70 g 4-pyridinecarboxylic acid, and 9.76 g dimethylaminopyridine were dissolved in 500 mL CH2Cl2 and cooled to 5° C. 33.01 g DCC was dissolved in 250 mL CH2Cl2 and added to the above mixture within 2 h. The reaction mixture was stirred for 48 h at rt. 200 mL water was added and the mixture is stirred for 2 h at rt. The precipitate was filtered off and the organic phase was extracted two times with 500 mL water. The organic solvent was evaporated in vacuo. The crude product was then submitted to column chromatography (SiO2, ethyl acetate/methanol 99:1) to give 46.2 g (86%) of 1 g as a white solid. MS (ESI): m/z (%): 334 (MH+), 336 ([M−H]+).

Workup

additionadded to the above mixture within 2 h
stirringthe mixture is stirred for 2 h at rt
filtrationThe precipitate was filtered off
extractionthe organic phase was extracted two times with 500 mL water
customThe organic solvent was evaporated in vacuo
customto give 46.2 g (86%) of 1 g as a white solid

Sources & evidence

ORD record: ord-3798824f7d194f63aa69ff1bbb03d097
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06887864B2

Reaction notes

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