Sodium Carbonate → HCID 66902736, compound

HRID 2242310Notes

Reaction equation

HRID 2242310 reaction equation
[C:1]1([C@H:7]([NH:9][C@@:10]2([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:15][C@H:14](O)[CH:13]3[CH:11]2[C@H:12]3[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COCCN(S(F)(F)[F:37])CCOC.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[C:1]1([C@H:7]([NH:9][C@@:10]2([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:15][C@@H:14]([F:37])[CH:13]3[CH:11]2[C@H:12]3[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 66902295HCID 66902295, compound

Product 1

HCID 66902736HCID 66902736, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-[((1R)-1-phenylethyl)amino](2S,4S,6R)-2-(ethoxycarbonyl)-4-hydroxybicyclo[3.1.0]hexane-6-carboxylate (59.0 g crude, 0.163 mol) in CH2Cl2 (690 mL) at −20° C. is added Deoxo-Fluor® (45.1 mL, 0.245 mol) over 15 minutes, maintaining the temperature between −15 and −20° C. The mixture is stirred for 20 minutes at this temperature and at 0° C. for 15 minutes before aqueous 15% Na2CO3 (650 ml) is slowly added while maintaining the temperature below 10° C. The layers are separated and the aqueous layer back extracted with CH2Cl2 (150 mL). The combined organic layers are dried (Na2SO4) and concentrated to a brown oil (73 g). The oil is purified on a pad of silica gel (400 g) eluting with EtOAc/heptane (1:6) to afford the title compound as a yellow oil (49.7 g, 84%).

Workup

  1. temperaturemaintaining the temperature between −15 and −20° C
  2. additionis slowly added
  3. temperaturewhile maintaining the temperature below 10° C
  4. customThe layers are separated
  5. extractionthe aqueous layer back extracted with CH2Cl2 (150 mL)
  6. dry with materialThe combined organic layers are dried (Na2SO4)
  7. concentrationconcentrated to a brown oil (73 g)
  8. customThe oil is purified on a pad of silica gel (400 g)
  9. washeluting with EtOAc/heptane (1:6)

Sources & evidence

ORD record
ord-83683091c6074d64bb3662f9bedb431b
Source dataset
uspto-grants-2010_03
Patent number
US07671082B2

Reaction notes

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