Diisopropylethylamine → Morpholine-4-carboxylic acid[(r)-1-(2,6-dihydroxy-cyclohexylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide
Reaction equation
[NH2:1][CH:2]1[CH:7]([OH:8])[CH2:6][CH2:5][CH2:4][CH:3]1[OH:9].C(N(C(C)C)CC)(C)C.[N:19]1([C:25]([NH:27][C@@H:28]([CH2:32][S:33]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:35])=[O:34])[C:29](O)=[O:30])=[O:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[OH:9][CH:3]1[CH2:4][CH2:5][CH2:6][CH:7]([OH:8])[CH:2]1[NH:1][C:29]([C@@H:28]([NH:27][C:25]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:26])[CH2:32][S:33]([CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)(=[O:35])=[O:34])=[O:30]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-amino-cyclohexane-1,3-diol (0.55 g) in dimethylformamide (30 ml) was treated with diisopropylethylamine (1.6 ml, 9.2 mmol). After stirring at room temperature for 5 minutes the mixture was treated with (R)-2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acid (1.73 g, 4.86 mmol) followed by HATU (1.68 g, 4.42 mmol). This mixture was stirred at room temperature overnight and then evaporated. The residue was subjected to flash chromatography on silica eluting with ethyl acetate and then a mixture of ethyl acetate and methanol to give morpholine-4-carboxylic acid [(R)-1-(2,6-dihydroxy-cyclohexylcarbamoyl)-2-phenylmethanesulfonyl-ethyl]-amide as a white solid (210 mg). MS: 470 (MH+).
Workup
- stirringThis mixture was stirred at room temperature overnight
- customevaporated
- additiona mixture of ethyl acetate and methanol
Sources & evidence
- ORD record
- ord-82b8d578b0014890a5bb0029e1078d47
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07196099B2
Reaction notes
Loading…