Hydrochloric Acid → HCID 54420046, compound
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][S:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].ClC(OCC(C)C)=O.C(N(CC)CC)C.[CH3:32][NH:33][C@H:34]([C:36]([OH:38])=[O:37])[CH3:35].Cl>C1COCC1.O>[CH3:32][N:33]([C:14](=[O:16])[CH2:13][CH2:12][S:11][S:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[C@H:34]([C:36]([OH:38])=[O:37])[CH3:35]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of 3-(4-nitrophenyldithio)-propanoic acid (5b) (0.100 g, 0.386 mmol) in dry THF (10 mL) at −40° C. under argon was added isobutyl chloroformate (0.053 g, 0.386 mmol) and triethylamine (0.039 g, 0.38 mmol) and the reaction stirred at 0° C. for one hour. An aqueous solution (5 mL) of N-methyl-L-alanine (0.040 g, 0.386 mmol) and triethylamine (0.039 g, 0.386 mmol) was then added and the mixture stirred at 0° C. for five hours. The mixture was diluted with water (50 mL), acidified (aqueous HCl), and extracted with ethyl ether (3×25 mL). The combined organic layers were dried (Na2SO4), and the solvent evaporated under reduced pressure. The residue was chromatographed over silica gel eluting with methylene chloride/ethyl acetate to yield 0.048 g (36%) yellow crystals: mp 74-77° C. 1H NMR (CDCl3) δ1.4 (3H, d), 2.6-3.4 (4H, m), 2.9 (3H, s), 5.1 (1H, q), 7.6-8.3 (4H, 2d).
Workup
- stirringthe mixture stirred at 0° C. for five hours
- extractionextracted with ethyl ether (3×25 mL)
- dry with materialThe combined organic layers were dried (Na2SO4)
- customthe solvent evaporated under reduced pressure
- customThe residue was chromatographed over silica gel eluting with methylene chloride/ethyl acetate
Sources & evidence
- ORD record
- ord-4f4acceb2b134d0eb96b54d29d28d5b7
- Source dataset
- uspto-grants-2006_06
- Patent number
- USRE039151E1
Reaction notes
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