4-Methylmorpholine → HCID 18790164, compound

HRID 1107116Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([C:12]([CH2:27][CH3:28])([CH2:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:13][C:14](O)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.[CH2:30]([O:37][NH2:38])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[CH2:30]([O:37][NH:38][C:14](=[O:15])[CH2:13][C:12]([S:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)(=[O:10])=[O:11])([CH2:27][CH3:28])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 0.4 g (0.99 mmol) of 3-(4-methoxyphenylsulfonyl)-3-ethyl-7-phenylheptanoic acid in 50 mL of methylene chloride is added 0.47 g (2.96 mmol, 3 eq) of O-benzyl-hydroxylamine hydrochloride, 0.13 g (0.247 mmol) of HOBT, 0.54 mL (4.94 mmol, 5 eq) of n-Methylmorpholine (NMM), and 0.25 g (1.28 mmol, 1.3 eq) of EDCl. After stirring for 18 hours at 25° C. the reaction is partitioned between methylene chloride and 1 N HCl. The organic layer is dried over anhydrous Na2SO4 then concentrated in vacuo. Purification by flash silica gel chromatography afforded 0.463 g (92%) of N-benzyloxy-3-(4-methoxyphenylsulfonyl)-3-ethyl-7-phenylheptanamide in the form of a colorless oil.

Workup

customis partitioned between methylene chloride and 1 N HCl
dry with materialThe organic layer is dried over anhydrous Na2SO4
concentrationthen concentrated in vacuo
customPurification by flash silica gel chromatography

Sources & evidence

ORD record: ord-ae3cf789d46f4f84948f048bf0343ab8
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057369

Reaction notes

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