Hydrochloric Acid → HCID 68620921, compound
Reaction equation
[C:1]1([C@@H:7]([NH:14][C:15]([C@H:17]2[N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19][S:18]2)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:29].[OH-].[Na+]>C(Cl)Cl>[ClH:29].[C:1]1([C@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[NH:14][C:15]([C@H:17]2[NH:21][CH2:20][CH2:19][S:18]2)=[O:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
In a 6 L 4-neck flask, was added a solution containing a compound of general structure (V) (Intermediate 6, 60 g g, 150.18 mmol), e.g., tert-butyl (2S)-2-({[(R)-phenyl(pyridin-2-yl)methyl]amino}carbonyl)-1,3-thiazolidine-3-carboxylate, in DCM under argon atmosphere (1250 ml). At −30° C., a solution of HCl conc. (627 mL, 7509 mmol) was added slowly during a period of 40 minutes. The reaction mixture was stirred at −30° C. for 3 h 30. The reaction was kept at −30° C. and a solution of 1 L of NAOH 1M was added followed by 1250 mL of NaOH 5M so that to obtain pH=5. The last 50 mL of 5M NaOH solution were added at −10° C. due to formation if ice in the flask. The slurry was extracted with DCM (5×500 mL) and dried over MgSO4 and evaporated to almost dryness. The desired product, e.g., (2S)—N—[(R)-phenyl(pyridin-2-yl)methyl]-1,3-thiazolidine-2-carboxamide hydrochloride, was isolated and used for the next step without further purification and shows no trace of racemisation.
Workup
- additionIn a 6 L 4-neck flask, was added a solution
- customwas kept at −30° C.
- additiona solution of 1 L of NAOH 1M was added
- customto obtain pH=5
- extractionThe slurry was extracted with DCM (5×500 mL)
- dry with materialdried over MgSO4
- customevaporated to almost dryness
Sources & evidence
- ORD record
- ord-9aa865c5f8614372921a1d47c135bd7f
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415480B2
Reaction notes
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