Dimethyl Sulfoxide → HCID 468478, compound
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16](=[O:34])[NH:17][C@@H:18]([CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:19]([N:21]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22]1)=[O:20])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[C:11]([O:15][C:16](=[O:34])[NH:17][C@@H:18]([CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:19](=[O:20])[N:21]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22]1)([CH3:14])([CH3:12])[CH3:13]Participants
Conditions
- Temperature
- 25 °C
Procedure
A solution of dimethyl sulfoxide (4.07 g, 52 mmol) and oxalyl chloride (3.61 g, 28 mmol) were added slowly in that order to dichloromethane (50 ml) at −78° C. (S)-[1-Benzyl-2-(3-hydroxy-pyrrolidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (24 mmol) in dichloromethane (30 ml) was added to the above solution via canula, the reaction temperature brought to −30° C. for 0.5 hours, then lowered to −78° C. followed by the additon of triethylamine (118 mmol). The reaction was then warmed to 25° C., diluted with ethyl acetate, washed three times with 1:1 saturated NaHCO3/brine, the organics dried over MgSO4 and concentrated. The resulting foam was purified by chromatography on silica gel eluted with 30, 40 and 50% ethyl acetate in hexanes to give a light yellow foam (7.5 g, 95% yield).
Workup
- additionwas added to the above solution via canula
- customlowered to −78° C.
- washwashed three times with 1:1 saturated NaHCO3/brine
- dry with materialthe organics dried over MgSO4
- concentrationconcentrated
- customThe resulting foam was purified by chromatography on silica gel
- washeluted with 30, 40 and 50% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-5ed0a126c4684ccc86dff01b7586bff8
- Source dataset
- uspto-grants-2001_08
- Patent number
- US06277877B1
Reaction notes
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