Tetrahydrofuran → HCID 86595499, compound
Reaction equation
[Cl:1][CH2:2][C:3]1C(C(O)=O)=CC=[CH:7][CH:8]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:24][C@@H:25]([C:28]([N:30]1[C@H:34]([C:35]([OH:37])=[O:36])[CH2:33][CH2:32][CH2:31]1)=[O:29])[CH2:26][SH:27].[CH2:38]1[CH2:42][O:41][CH2:40][CH2:39]1>>[Cl:1][CH2:2][C:3]1[CH:40]=[CH:39][C:38]([C:42]([S:27][CH2:26][C@@H:25]([CH3:24])[C:28]([N:30]2[CH2:31][CH2:32][CH2:33][C@H:34]2[C:35]([OH:37])=[O:36])=[O:29])=[O:41])=[CH:7][CH:8]=1Participants
Procedure
α-chloro-toluic acid (9.0 g, 0.0528 Mol) and carbonyldiimidazole (10.3 g, 0.0634 Mol) were dissolved in THF (100 ml) and stirred overnight at room temperature. Then TEA was added (7.4 ml. 0.0528 Mol) and to this reaction mixture a solution of captopril (11.5 g, 0.0528 Mol) in THF (20 ml) was added dropwise and the reaction was stirred overnight at room temperature. The mixture was then partitioned between KHSO4 10% and EtOAc (120 ml). The organic layer was separated and the aqueous phase was extracted with EtOAc (2×60 ml). The combined organic phases were washed with water (3×60 ml), dried over sodium sulphate and evaporated under reduced pressure affording 14.1 g of 1-[(2S)-3-(4-chloromethylbenzoyl)mercapto-2-methyl-1-oxopropyl]-L-proline as a white solid used for the next step without further purification.
Workup
- additionThen TEA was added (7.4 ml. 0.0528 Mol)
- stirringthe reaction was stirred overnight at room temperature
- customThe mixture was then partitioned between KHSO4 10% and EtOAc (120 ml)
- customThe organic layer was separated
- extractionthe aqueous phase was extracted with EtOAc (2×60 ml)
- washThe combined organic phases were washed with water (3×60 ml)
- dry with materialdried over sodium sulphate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-6beb17abe6324a9e9032ae71c631e4f8
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07169805B2
Reaction notes
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