Water → HCID 77582160, compound

HRID 1512718Notes

Reaction equation

HRID 1512718 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[C:33]([O:37][CH3:38])[C:34]=1[O:35][CH3:36])[C:6]([O:8][CH2:9][C:10]([N:19](C(OC(OC(=O)C(C)C)C)=O)[CH3:20])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:11][CH3:12])=[O:7].[OH2:39]>>[CH3:38][O:37][C:33]1[CH:32]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:34]=1[O:35][CH3:36])[C:6]([O:8][CH2:9][C:10]([NH:19][CH2:20][C:9]([O:8][CH2:6][C:5]1[CH:32]=[CH:33][C:34]([O:35][CH3:36])=[CH:3][CH:4]=1)=[O:39])([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:11][CH3:12])=[O:7]

Participants

3

Reactant 2

HCID 962WaterHCID 76619031HCID 76619031, compound

Product 1

HCID 77582160HCID 77582160, compound

Procedure

10 ml water is added to the mixture. The product is extracted with ethyl acetate (3 times 10 mL) then the organic phase is washed successively with water and a saturated solution of sodium chloride (15 mL). The organic phases are dried over Na2SO4, filtered then concentrated to dryness in order to produce a brown oil. The oil is purified by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate: 85/15) in order to produce 105 mg of the expected product (S) 2-[(1-isobutyryloxy-ethoxycarbonyl)-methyl-amino]-2-phenyl-n-butyl 3,4,5-trimethoxy-benzoate in the form of a colourless oil (yield=15%).

Workup

  1. extractionThe product is extracted with ethyl acetate (3 times 10 mL)
  2. washthe organic phase is washed successively with water
  3. dry with materialThe organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthen concentrated to dryness in order
  6. customto produce a brown oil
  7. customThe oil is purified by flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate: 85/15) in order

Sources & evidence

ORD record
ord-678e02ff060144a7970081ca182a2321
Source dataset
uspto-grants-2012_07
Patent number
US08217075B2

Reaction notes

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