Sodium Ascorbate → HCID 69272714, compound

HRID 2219894Notes

Reaction equation

HRID 2219894 reaction equation
[N:1]([C@H:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([F:21])[CH2:17][CH2:16]3)=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5]1)=[N+:2]=[N-:3].[CH:22]1[C:34]2[CH:33]([CH2:35][O:36][C:37]([C@H:39]([CH2:44][C:45]#[CH:46])[C:40]([O:42][CH3:43])=[O:41])=[O:38])[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:26]=2[CH:25]=[CH:24][CH:23]=1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.O>[CH:31]1[C:32]2[CH:33]([CH2:35][O:36][C:37]([CH:39]([CH2:44][C:45]3[N:3]=[N:2][N:1]([C@H:4]4[C:13]5[C:8](=[CH:9][C:10]([CH2:14][N:15]6[CH2:16][CH2:17][CH:18]([F:21])[CH2:19][CH2:20]6)=[CH:11][CH:12]=5)[O:7][CH2:6][CH2:5]4)[CH:46]=3)[C:40]([O:42][CH3:43])=[O:41])=[O:38])[C:34]3[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:27]=2[CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 23667548Sodium AscorbateHCID 59771809HCID 59771809, compoundHCID 86604888HCID 86604888, compound

Product 1

HCID 69272714HCID 69272714, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

To a stirred mixture of (R)-1-((4-azido-3,4-dihydro-2H-chromen-7-yl)methyl)-4-fluoropiperidine (0.83 g, 2.9 mmol) and (R)-methyl 2-(((9H-fluoren-9-yl)methoxy)-carbonyl)pent-4-ynoate (1.0 g, 2.9 mmol) in t-BuOH/H2O (1:1, 40 mL) was added a solution of sodium ascorbate (30 mg, 0.14 mmole) in H2O (300 μL), followed by CuSO4.5H2O (7 mg, 0.03 mmol) in H2O (300 μL). The reaction mixture was stirred for 72 h at RT. The reaction mixture was concentrated, extracted with CH2Cl2 (3×), dried over MgSO4, and concentrated. The residue was purified by SiO2 (2% MeOH/CH2Cl2) to give the title compound. MS (m/z): 640.4 (m+H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by SiO2 (2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-fd4d15e293234a43a9b32af4db7192bf
Source dataset
uspto-grants-2008_08
Patent number
US07414134B2

Reaction notes

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