Benzyl chloroformate → HCID 69462213, compound

HRID 889572Notes

Reaction equation

HRID 889572 reaction equation
[NH2:1][C@H:2]([C@@H:5]([OH:22])[C@H:6]([OH:21])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:3][OH:4].C([O-])(O)=O.[Na+].Cl[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30].C(Cl)Cl.CO>O1CCOCC1.CCOC(C)=O>[CH2:32]([O:31][C:29]([NH:1][C@H:2]([C@@H:5]([OH:22])[C@H:6]([OH:21])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:3][OH:4])=[O:30])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 11099168HCID 11099168, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 69462213HCID 69462213, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

(Ozinskas et al., J. Org. Chem. 1986. 51: 4057-5050). To a suspension of starting material 31 (Cosmoferm B. V., Delft, Netherlands) (6.35 g, 20 mmol) in aqueous NaHCO3 (1 N, 80 ml, 4 equiv.) and 1,4-dioxane (30 ml) was added benzyl chloroformate (3.31 ml, 1.1 equiv.). The reaction mixture was stirred at rt overnight, whereupon t.l.c (only ethyl acetate or DCM-MeOH 5:1) indicated the reaction was finished. The suspension was diluted with EtOAc and poured onto water. After separation, the aqueous phase was extracted with EtOAc (3×). The combined organic solutions were washed aqueous NH4Cl, brine, dried over Na2SO4, and concentrated to afford a residue. The residue was purified by flash column chromatography (Petroether-EtOAc, 2:1 to only EtOAc) to provide compound 32 (8.13 g, 90%) as a white solid.

Workup

  1. additionpoured onto water
  2. customAfter separation
  3. extractionthe aqueous phase was extracted with EtOAc (3×)
  4. washThe combined organic solutions were washed aqueous NH4Cl, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto afford a residue
  8. customThe residue was purified by flash column chromatography (Petroether-EtOAc, 2:1 to only EtOAc)

Sources & evidence

ORD record
ord-ecfc1dbbe5964e798a918e40c62921dc
Source dataset
uspto-grants-2012_08
Patent number
US08252909B2

Reaction notes

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