Trifluoroacetic acid → HCID 117886821, compound
Reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:6]([NH:8][C@H:9]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])[C@@H:3]([CH3:5])[OH:4].FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[NH2:1][C@H:2]([C:6]([NH:8][C@H:9]([C:14]([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13])=[O:7])[C@@H:3]([CH3:5])[OH:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Compound 1 from previous step (27.5 g, 65.084 mmol) was dissolved in dichloromethane (215 mL) and the solution was treated with trifluoroacetic acid (149.9 g) which was added within 5 minutes. The reaction mixture was stirred for additional 25 minutes at room temperature to complete the reaction. For work-up, the solution was diluted with dichloromethane (300 mL) and was treated slowly with half saturated aq. Na2CO3-solution (660 mL). The biphasic mixture was intensively stirred for 15 minutes and the phases were separated. The aqueous phase was extracted with dichloromethane (300 mL) and the organic phases were combined. The combined organic phase was washed with water (300 mL) and the solvent was evaporated under reduced pressure at 40-45° C. to obtain 21.72 g crude product, Thr-Leu-OBzl (100% crude yield) as foam. The crude product (compound 2) was sufficiently pure to use for the next step without additional purification.
Workup
- additionwas added within 5 minutes
- customthe reaction
- stirringThe biphasic mixture was intensively stirred for 15 minutes
- customthe phases were separated
- extractionThe aqueous phase was extracted with dichloromethane (300 mL)
- washThe combined organic phase was washed with water (300 mL)
- customthe solvent was evaporated under reduced pressure at 40-45° C.
Sources & evidence
- ORD record
- ord-45b334ef54954f338dc0bee4dc35795c
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067978B2
Reaction notes
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