HCID 10404865, compound → HCID 14523252, compound

HRID 1162843Notes

Reaction equation

HRID 1162843 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([C:19](N(OC)C)=[O:20])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[CH2:1]([O:8][CH2:9][CH:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH:19]=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10404865HCID 10404865, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14523252HCID 14523252, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A cold (10° C.) solution of O-benzyl-N1-methoxy-N1-methyl-N2-(tert-butoxycarbonyl)serinamide (6.27 g, 18.5 mmol) in diethyl ether (312 mL) was treated in portions with LAH (780 mg, 20.6 mmol). The reaction was stirred under inert atmosphere for 30 min and quenched at 0° C. by the addition of a solution of KHSO4 (16 g) in water (75 mL). The mixture was diluted with 1 M aqueous HCl (60 mL), and the organic layer was washed with brine, dried over MgSO4 and concentrated in vacuo to a yellow oil. Purification by silica gel chromatography (10% to 50% EtOAc/hexanes) afforded the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 9.64 (s, 1H), 7.38-7.26 (m, 5H), 5.42 (d, J=5.0 Hz, 1H), 4.51 (dd, J=12.0, 19.5 Hz, 2H), 4.32 (d, J=4.01-3.99 (m, 1H), 3.73-3.70 (m, 1H), 1.46 (s, 9H). ES MS (M+1−100, for loss of BOC group)=180.1.

Workup

  1. customquenched at 0° C. by the addition of a solution of KHSO4 (16 g) in water (75 mL)
  2. additionThe mixture was diluted with 1 M aqueous HCl (60 mL)
  3. washthe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo to a yellow oil
  6. customPurification by silica gel chromatography (10% to 50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a0de3b5d0f81477b858024bee3748fed
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

Loading…