Ethyl formate → HCID 86607895, compound

HRID 736794Notes

Reaction equation

FC(F)(F)[C:3](O)=[O:4].[C:8]([O:12][NH:13][C:14]([C@:16]1([OH:45])[C@H:21]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:37]=[C:36]([CH3:44])[CH:35]=3)=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:20][CH2:19][NH:18][CH2:17]1)=[O:15])([CH3:11])([CH3:10])[CH3:9].C(N(C(C)C)CC)(C)C.C(OCC)=O>CO>[C:8]([O:12][NH:13][C:14]([C@:16]1([OH:45])[C@H:21]([NH:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]3[C:43]4[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:37]=[C:36]([CH3:44])[CH:35]=3)=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH2:20][CH2:19][N:18]([CH:3]=[O:4])[CH2:17]1)=[O:15])([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 46 °C

Procedure

(3R,4R)-N-tert-Butoxy-3-hydroxy-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide trifluoroacetic acid salt (250 mg, 0.32 mmol) was dissolved in methanol (1 mL) and diisopropylethylamine (0.23 mL, 1.3 mmol, 4 eq) was added, followed by ethyl formate (5 mL, excess). The reaction was heated at 46° C. for 5 h, and then concentrated in vacuo. The residue was triturated with ether to yield 112 mg (62%) of (3R,4R)-N-tert-butoxy-1-formyl-3-hydroxy-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide as white waxy solid. MS: (M+H)+=571.1.

Workup

concentrationconcentrated in vacuo
customThe residue was triturated with ether

Sources & evidence

ORD record: ord-e7d8d6cf64374b9ab88293732366cc5e
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

Loading…