4-Methylmorpholine → HCID 69236191, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:9]([C:15]([N:17]1[CH2:21][CH2:20][S:19][CH2:18]1)=[O:16])[CH2:10][CH2:11][C:12](=O)[OH:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+].C(OC(N(C(O)CCCC(C1NCCS1)=O)C(OC(C)(C)C)=O)=O)(C)(C)C>O1CCCC1.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([CH:9]([CH2:10][CH2:11][CH2:12][OH:13])[C:15]([N:17]1[CH2:21][CH2:20][S:19][CH2:18]1)=[O:16])[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
9
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- -20 °C
Procedure
3-[N,N-Di-(tert-butyloxycarbonyl)-L-glutamyl]thiazolidine (912 mg, 2.2 mmol) was dissolved in tetrahydrofuran (30 mL). This solution was cooled to −20° C., N-methylmorpholine (300 mg, 2.96 mmol) and isobutyl chloroformate (387 mg, 2.83 mmol) were added. After 20 mins at −20° C. the reaction mixture was added to a solution of sodium borohydride (182 mg, 4.8 mmol) in water (5 mL) at 0° C. After 1 hour the reaction mixture was diluted with ethyl acetate (150 mL). This solution was washed with water (1×20 mL) and brine (1×20 mL), dried (Na2SO4) and evaporated in vacuo to give a colourless oil identified as 3-[2-(N,N-di-(tert-butyloxycarbonyl)amino-5-hydroxy-pentanoyl]thiazolidine (800 mg, 2.0 mmol, 92%).
Workup
- washThis solution was washed with water (1×20 mL) and brine (1×20 mL)
- dry with materialdried (Na2SO4)
- customevaporated in vacuo
- customto give a colourless oil
Sources & evidence
- ORD record
- ord-0f51b3fe2e984ee88ab90da1d2fb1e6f
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07335677B2
Reaction notes
Loading…