4-Morpholinecarbonyl chloride → (2s)-2-[(Morpholine-4-carbonyl)-amino]-3-naphthalen-1-yl-propionic acid
Reaction equation
[CH:1]1[CH:6]=[C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][C@H:12]([NH2:16])[C:13]([OH:15])=[O:14])[C:4]2=[CH:3][CH:2]=1.[N:17]1([C:23](Cl)=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>[OH-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>[N:17]1([C:23]([NH:16][C@@H:12]([CH2:11][C:10]2[C:4]3[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=3)[CH:7]=[CH:8][CH:9]=2)[C:13]([OH:15])=[O:14])=[O:24])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1Participants
5
Procedure
To a solution of L-1-naphthylalanine (215 mg, 1 mmol) (Peptech Corp.) in 5 mL 1N NaOH and 0.5 mL saturated Na2CO3 (resulting solution at pH 10) was added morpholine-4-carbonyl chloride (150 mg, 1.0 mmol) dissolved in 5 mL. Afterwards, the reaction mixture was stirred at room temperature for 2 h. The alkaline solution was extracted once with ether (10 mL) and the aqueous phase was acidified with 1N HCl. This was extracted twice with 20 mL EtOAc, and the combined organic phases were washed with 50 mL 1N HCl. The organic phase was dried over Na2SO4, filtered and evaporated to an oil, which solidifies to yields 125 mg (38%) of the desired material. This compound was used as such in the next step.
Workup
- dissolutiondissolved in 5 mL
- extractionThe alkaline solution was extracted once with ether (10 mL)
- extractionThis was extracted twice with 20 mL EtOAc
- washthe combined organic phases were washed with 50 mL 1N HCl
- dry with materialThe organic phase was dried over Na2SO4
- filtrationfiltered
- customevaporated to an oil, which
Sources & evidence
- ORD record
- ord-8d2138d3de994fcfbc4782889e7a20bb
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07388008B2
Reaction notes
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