Water → HCID 86674672, compound
Reaction equation
[CH2:1]([O:8][C@@H:9]([CH2:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:10][C:11]1([S:14]([O:17]C(C)C)(=[O:16])=[O:15])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([S-])#N.[K+].O>C1COCC1>[CH2:1]([O:8][C@@H:9]([CH2:21][O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:10][C:11]1([S:14]([OH:17])(=[O:16])=[O:15])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of (R)-isopropyl 1-(2,3-bis(benzyloxy)propyl)cyclopropane-1-sulfonate (460 g) and KSCN (170 g) in THF 2.2 L) and water (2.2 L) at 25° C. was refluxed for approximately 24 hours at 90° C. until HPLC analysis showed that the reaction had gone to completion. The reaction mixture was concentrated to about 2 L at 40° C. and extracted with MTBE (1.5 L (×3)). The organic layer was discarded and the aqueous layer was neutralized to pH 14 with KOH (30 g) in water (100 mL) and cooled to −5° C. The mixture was neutralized to a pH of between 2 and 3 with concentrated HCl (205 mL) and extracted with ETOAc (2 L (×2)). The combined organic layers was dried over Na2SO4 for approximately 16 hours, filtered and concentrated to dryness to give the product as a deep red oil (265 g).
Workup
- concentrationThe reaction mixture was concentrated to about 2 L at 40° C.
- extractionextracted with MTBE (1.5 L (×3))
- temperaturecooled to −5° C
- extractionextracted with ETOAc (2 L (×2))
- dry with materialThe combined organic layers was dried over Na2SO4 for approximately 16 hours
- filtrationfiltered
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-3ccb9ef663084d34a8284c06bd2edf21
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470878B2
Reaction notes
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