(Diethylamino)sulfur trifluoride → Methyl 4-[bis(tert-Butoxy)phosphoryl-fluoromethyl]-N-(benzyloxycarbonyl)-D,L-phenylalaninate

HRID 2260006Notes

Reaction equation

HRID 2260006 reaction equation
CCN(S(F)(F)[F:7])CC.[C:10]([O:14][P:15]([CH:22](O)[C:23]1[CH:45]=[CH:44][C:26]([CH2:27][CH:28]([C:40]([O:42][CH3:43])=[O:41])[NH:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[CH:25][CH:24]=1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH3:13])([CH3:12])[CH3:11]>C(Cl)(Cl)Cl.[Cl-].[Na+].O>[C:10]([O:14][P:15]([CH:22]([F:7])[C:23]1[CH:45]=[CH:44][C:26]([CH2:27][CH:28]([C:40]([O:42][CH3:43])=[O:41])[NH:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[CH:25][CH:24]=1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 10392366Methyl 4-[bis(tert-butoxy)phosphorylhydroxymethyl]-N-(benzyloxycarbonyl)-D,L-phenylalaninate

Product 1

HCID 10369964Methyl 4-[bis(tert-Butoxy)phosphoryl-fluoromethyl]-N-(benzyloxycarbonyl)-D,L-phenylalaninateYield 117%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To DAST (0.15 mL, 1.1 mmol) in anhydrous CHCl3 (0.6 mL) at -78° C. was slowly added compound 9 (536 mg, 1.0 mmol) in CHCl3 (2.0 mL). After 10 minutes, the reaction mixture was warmed to ambient temperature and stirred (20 minutes). The mixture was slowly diluted with brine (10 mL) then extracted with CHCl3 (2×10 mL) and the combined extracts dried (MgSO4) and evaporated under reduced pressure to yield crude 20 (629 mg). Purification by silica gel chromatography afforded pure 20 as a syrup (295 mg, 55%).

Workup

  1. customat -78° C.
  2. extractionthen extracted with CHCl3 (2×10 mL)
  3. dry with materialthe combined extracts dried (MgSO4)
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e6ec17eafc704b688a3dfc9c243fef37
Source dataset
uspto-grants-1995_12
Patent number
US05475129

Reaction notes

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