HCID 11521987, compound → HCID 53784530, compound

HRID 863190Notes

Reaction equation

HRID 863190 reaction equation
[CH2:1]([O:3][C:4]([NH:6][C@H:7]([C:15](N(C)OC)=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:1]([O:3][C:4]([NH:6][C@H:7]([CH:15]=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 11521987HCID 11521987, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 53784530HCID 53784530, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To 56 mg (200 μmole) (12), prepared in Step 1, above, was added 2 mL of dry Et2O, and the solution was cooled to 0° C. Lithium aluminum hydride (9.5 mg, 50 μmole, 1.25 eq. H-) was added, and the reaction was monitored by TLC. After 2 h the reaction was quenched with ca. 4 mL ethyl acetate and the solution stirred for 40 min. The organic layer was washed 2× with dilute HCl, 2× with saturated NaHCO3, and 1× with brine. The organic layer was dried with Na2SO4, filtered, and the filtrate evaporated. The residue was pumped on high vacuum overnight, then purified by flash silica gel chromatography to give the title compound. NMR (300 MHz, CDCl3): δ 9.60 (s, CHO, 1H), 7.20 (m, Ph, 5H), 4.45 (br dd, Phe-α, 1H), 4.08 (q, CH3CH2OCO, 2H), 3.08 (d, Phe-β, 2H), 1.20 (t, CH3CH2OCO, 3H).

Workup

  1. customAfter 2 h the reaction was quenched with ca. 4 mL ethyl acetate
  2. washThe organic layer was washed 2× with dilute HCl, 2× with saturated NaHCO3, and 1× with brine
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customwas pumped on high vacuum overnight
  7. custompurified by flash silica gel chromatography

Sources & evidence

ORD record
ord-1055f6bbd42b470a95e43b7516014e28
Source dataset
uspto-grants-1998_02
Patent number
US05719296

Reaction notes

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