Water → HCID 77582160, compound

HRID 1512719Notes

Reaction equation

HRID 1512719 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([O:39][CH3:40])[C:36]=1[O:37][CH3:38])[C:6]([O:8][CH2:9][C:10]([N:19](C(OC(OC(=O)CNC(=O)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].[OH2:41]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([O:39][CH3:40])[C:36]=1[O:37][CH3:38])[C:6]([O:8][CH2:9][C:10]([NH:19][CH2:20][C:9]([O:8][CH2:6][C:5]1[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[CH:3][CH:4]=1)=[O:41])([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 76619033HCID 76619033, compound

Product 1

HCID 77582160HCID 77582160, compound

Procedure

20 ml water is added to the mixture. The product is extracted with ethyl acetate (3 times 50 mL) then the organic phase is washed successively with water and a saturated solution of sodium chloride (10 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: 3/7) in order to produce 200 mg of the expected product (S) 2-{[1-(2-acetylamino-acetoxy)-ethoxycarbonyl]-methyl-amino}-2-phenyl-n-butyl 3,4,5-trimethoxy-benzoate in the form of a brown solid (yield=7%).

Workup

  1. extractionThe product is extracted with ethyl acetate (3 times 50 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: 3/7) in order

Sources & evidence

ORD record
ord-bd6c985770b040dab76b230e0aad1737
Source dataset
uspto-grants-2012_07
Patent number
US08217075B2

Reaction notes

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