Ethyl Acetate → HCID 59243586, compound

HRID 425015Notes

Reaction equation

HRID 425015 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:20]([O:22][CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:21])[CH2:10][CH2:11][O:12][Si](C(C)(C)C)(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C>C(O)(=O)C.C1COCC1.O>[OH:12][CH2:11][CH2:10][C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:20]([O:22][CH:23]1[CH2:24][CH2:25][CH2:26][CH2:27]1)=[O:21]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 59243637HCID 59243637, compound

Product 1

HCID 59243586HCID 59243586, compound

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Conditions

Temperature
30 °C

Procedure

Cyclopentyl N-(tert-butoxycarbonyl)-O-[tert-butyl(dimethyl)silyl]-D-homoserinate (1.57 g, 3.9 mmol) was dissolved in acetic acid:THF:water (3:1:1, 100 ml). The reaction mixture was stirred at 30° C. for 16 hours for complete reaction. Ethyl acetate (200 ml) was added and washed with 1M Na2CO3, 1M HCl and brine. The ethyl acetate extracts were dried over magnesium sulphate and evaporated under reduced pressure to give the product as a clear oil which crystallised on standing (1.0 g, 95%).

Workup

  1. washwashed with 1M Na2CO3, 1M HCl and brine
  2. dry with materialThe ethyl acetate extracts were dried over magnesium sulphate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c614dae18db1483e8af32b9ba0c155c9
Source dataset
uspto-grants-2012_01
Patent number
US08106091B2

Reaction notes

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