Ammonium Chloride → (R)-benzyl 2,2-dimethyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-ylcarbamate
Reaction equation
CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.[NH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[S:50][C:51]([CH3:68])([CH3:67])[C@H:52]([NH:56][C:57]([O:59][CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)=[O:58])[C:53](O)=[O:54].[NH4+].[Cl-]>CN(C=O)C>[CH3:67][C:51]1([CH3:68])[S:50][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2[NH:43][C:53](=[O:54])[C@H:52]1[NH:56][C:57](=[O:58])[O:59][CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
DIEA (4.14 g, 5.6 mL, 32.0 mmol, Eq: 2) and (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP, 12.5 g, 24.0 mmol, Eq: 1.5) were added to (R)-3-(2-aminophenylthio)-2-(benzyloxycarbonylamino)-3-methylbutanoic acid (6 g, 16.0 mmol, Eq: 1.00) in DMF (200 mL). The mixture was stirred at RT overnight then heated to 80° C. for 3 h. The mixture was poured onto sat. NH4Cl and extracted with EtOAc. The combined extracts were washed with H2O, concentrated and the residue was purified by silica gel chromatography to give (R)-benzyl 2,2-dimethyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-ylcarbamate (3 g, 52%).
Workup
- temperaturethen heated to 80° C. for 3 h
- extractionextracted with EtOAc
- washThe combined extracts were washed with H2O
- concentrationconcentrated
- customthe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-1ba6f9f77a7d4e01bda23c1764143fd6
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09394263B2
Reaction notes
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