N-Methylpiperidine → HCID 14208556, compound

HRID 845328Notes

Reaction equation

[CH3:1][C:2]([CH3:28])([O:4][C:5]([NH:7][C@H:8]([C:17]([NH:19][C@@H:20]([C:25]([OH:27])=O)[CH2:21][CH2:22][S:23][CH3:24])=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)=[O:6])[CH3:3].CN1CCCCC1.[C:36]1([CH2:42][CH2:43][CH2:44][NH2:45])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)Cl>[CH3:3][C:2]([CH3:1])([O:4][C:5]([NH:7][C@H:8]([C:17]([NH:19][C@@H:20]([C:25]([NH:45][CH2:44][CH2:43][CH2:42][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:27])[CH2:21][CH2:22][S:23][CH3:24])=[O:18])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)=[O:6])[CH3:28]

Participants

Conditions

Temperature: 0 °C

Procedure

The title product of Example 2 (7.4 g, 17.9 mmol) dissolved in 75 ml of CH2Cl2 was flushed with Ar and cooled to 0° C. N-methylpiperidine (NMP, 2.2 ml, 17.9 mmol) was added to the reaction before it was cooled to -78° C. and charged with 2.5 ml (17.9 mmol) of IBCF. The reaction was allowed to warm to -15°, maintained at this temperature for 15 min., cooled to -78°, and charged with 2.4 g (17.9 mmol) of 3 phenylpropyl amine (PPA). The crude product, obtained after a reaction work up by the method of Example 1, was chromatographed on a Waters prep 500 using a Porasil cartridge eluting with 2% to 3% ethanol (EtOH)/CH2Cl2. The title product was obtained as a white solid (4.54 g).

Workup

customwas flushed with Ar
temperaturewas cooled to -78° C.
additioncharged with 2.5 ml (17.9 mmol) of IBCF
temperatureto warm to -15°
temperaturemaintained at this temperature for 15 min.
temperaturecooled to -78°
customThe crude product, obtained after a reaction work up by the method of Example 1
customwas chromatographed on a Waters prep 500 using a Porasil cartridge
washeluting with 2% to 3% ethanol (EtOH)/CH2Cl2

Sources & evidence

ORD record: ord-f5e799514a6844a4826c7a334d3bbbe5
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04757153

Reaction notes

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