Potassium bisulfate → HCID 22744159, compound

HRID 350614Notes

Reaction equation

HRID 350614 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH2:7][CH:8]([NH:15][C:16]([O:18][CH2:19][CH:20]1[C:32]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[C:9](N(OC)C)=[O:10])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].OS([O-])(=O)=O.[K+]>C(OCC)C>[C:1]([O:5][C:6](=[O:33])[CH2:7][CH:8]([NH:15][C:16]([O:18][CH2:19][CH:20]1[C:32]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH:9]=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydrideHCID 22134621HCID 22134621, compound

Product 1

HCID 22744159HCID 22744159, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of 3-(9H-Fluoren-9-ylmethoxycarbonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (4.57 g, 10.04 mmol) in Ethyl ether (30 mL) at −5° C. was added dropwise 0.5 equiv of 1.0M Lithium aluminum hydride (LAH) in ethyl ether (5.02 mL, 5.02 mmol). After stirring at −5° C. to room temperature for 1 hr, the reaction mixture was treated with 5% KHSO4 (200 mL), stirred for 5 min and then partitioned between EtOAc/water. The organic phase was washed with saturated NaCl solution (200 mL), dried over Na2SO4 and evaporated to dryness. The residue was purified by flask column chromatography on silica gel eluting with EtOAc/Hexane (20%) to give the title compound (2.18 g, 55%) as a clear oil. TLC (30% EtOAc/Hexane) Rf=0.35; 1HNMR (CDCl3) δ 9.65 (s, 1H), 7.77 (d, J=7.2 Hz, 2H), 7.50 (d, J=7.5 Hz, 2H), 7.41 (t, J=7.5 Hz, 2H), 7.33 (dt, J=7.5, 1.2 Hz, 2H), 5.88 (d, J=7.2 Hz, 1H), 4.50–4.36 (m, 2H), 4.24 (t, J=6.6 Hz, 1H), 3.54–3.45 (m, 1H), 3.00–2.93 (dd, J=17.4, 4.8 Hz, 1H), 2.82–274 (dd, J=17.7, 5.1s Hz, 1H), 1.45 (s, 9H). MS(ES) for C23H25NO5 (MW=395.45): positive 396 (MH+).

Workup

  1. stirringstirred for 5 min
  2. custompartitioned between EtOAc/water
  3. washThe organic phase was washed with saturated NaCl solution (200 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by flask column chromatography on silica gel eluting with EtOAc/Hexane (20%)

Sources & evidence

ORD record
ord-5d296ac1146b498980e2cb133c1e9625
Source dataset
uspto-grants-2007_02
Patent number
US07183260B2

Reaction notes

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