HCID 18707107, compound → HCID 54390265, compound

HRID 1421883Notes

Reaction equation

[N+](C1C=CC(O[C:11]([N:13]2[CH:17]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=3)[CH2:16][O:15][C:14]2=[O:26])=[O:12])=CC=1)([O-])=O.C(OC(=O)[N:33]([CH:40]1[CH2:45][CH2:44][C:43]([C:52]#[N:53])([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:42][CH2:41]1)[CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)(C)(C)C.CCCCCC.CCOC(C)=O>C1COCC1>[F:25][C:20]1[CH:19]=[C:18]([CH:17]2[CH2:16][O:15][C:14](=[O:26])[N:13]2[C:11]([N:37]2[CH2:36][CH2:35][CH:34]([NH:33][CH:40]3[CH2:41][CH2:42][C:43]([C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)([C:52]#[N:53])[CH2:44][CH2:45]3)[CH2:39][CH2:38]2)=[O:12])[CH:23]=[CH:22][C:21]=1[F:24]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 4-(3,4-difluoro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid 4-nitrophenyl ester (80 mg, 0.21 mmol) in 5 ml of THF was added (4-cyano-4-phenyl-cyclohexyl)-piperidin-4-yl-carbamic acid tert-butyl ester (150 mg, 0.40 mmol) in a portion and the resulting solution was stirred for 12 h at 25° C. Reaction mixture was concentrated in vacuo, yielding a yellow oil, which was subjected to column chromatography (50% Hexane/EtOAc) to provide the tert-butyl ester of the desired product as a colorless oil. The product obtained was dissolved in 5 ml of EtOAc and 1 ml of 1N HCl-Et2O to afford a white solid of the product as the HCl salt: mp 181-192 C; Anal. Calc. For C27H28F2N4O3.1.0HCl requires C, 61.70; H, 5.73; N, 10.28. Found: C, 59.48; H, 5.41; N, 10.34.

Workup

customReaction mixture
concentrationwas concentrated in vacuo
customyielding a yellow oil, which

Sources & evidence

ORD record: ord-4286f470ffbb4457a17d0f47dcde7a1e
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06080760

Reaction notes

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