Diisopropylethylamine → HCID 90016587, compound

HRID 920155Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:31])=[C:6]([C@:8]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=2[O:29][CH3:30])([CH3:18])[CH2:9][S:10][C:11]2([C:15]([OH:17])=O)[CH2:14][CH2:13][CH2:12]2)[CH:7]=1.C(N(C(C)C)CC)(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:31])=[C:6]([C@@:8]2([CH3:18])[N:19]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=3[O:29][CH3:30])[C:15](=[O:17])[C:11]3([CH2:14][CH2:13][CH2:12]3)[S:10][CH2:9]2)[CH:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of (R)-1-(2-(5-bromo-2-fluorophenyl)-2-(2,4-dimethoxybenzylamino) propylthio)cyclobutanecarboxylic acid (1.8 g, 3.51 mmol, Eq: 1.00) and diisopropylethylamine (1.36 g, 1.84 ml, 10.5 mmol, Eq: 3.0) in ethyl acetate (70.3 ml) was added at 23° C. 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate) (3.35 g, 3.08 ml, 5.27 mmol, Eq: 1.5). The colourless reaction solution was stirred at 23° C. for 16 hours. The reaction mixture was washed with sat. NaHCO3-sol., water and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give the crude and pure (R)-7-(5-bromo-2-fluorophenyl)-8-(2,4-dimethoxybenzyl)-7-methyl-5-thia-8-azaspiro[3.5]nonan-9-one (1.75 g, 3.54 mmol, 101% yield) as a white foam. MS (ISP): m/z=494.0 [M+H]+ and 496.4 [M+2+H]+.

Workup

washThe reaction mixture was washed with sat. NaHCO3-sol
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-27a3f5ec43d04aaa9145b5d8ac7bcb7a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273042B2

Reaction notes

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