Acetic Acid → (2S,3R)-3-(acetyloxy)-5-[4-(6-methoxypyridin-3-yl)phenyl]-2-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]pentanoic acid

HRID 84006Notes

Reaction equation

HRID 84006 reaction equation
N(C(OC(C)C)=O)=NC([O:5][CH:6](C)[CH3:7])=O.[OH:15][C@H:16]([CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:43]=[N:44][C:45]([O:48][CH3:49])=[CH:46][CH:47]=2)=[CH:38][CH:37]=1)[C@H:17]([CH2:21][CH2:22][N:23]1[C:28](=[O:29])[C:27]2[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=2[N:25]=[N:24]1)[C:18]([OH:20])=[O:19].C(P(CCCC)CCCC)CCC.C(O)(=O)C>O1CCCC1>[C:6]([O:15][C@H:16]([CH2:34][CH2:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[CH:43]=[N:44][C:45]([O:48][CH3:49])=[CH:46][CH:47]=2)=[CH:40][CH:41]=1)[C@H:17]([CH2:21][CH2:22][N:23]1[C:28](=[O:29])[C:27]2[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=2[N:25]=[N:24]1)[C:18]([OH:20])=[O:19])(=[O:5])[CH3:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 13831TributylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66671252(2S,3R)-3-hydroxy-5-[4-(6-methoxypyridin-3-yl)phenyl]-2-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]pentanoic acid

Product 1

HCID 67182848(2S,3R)-3-(acetyloxy)-5-[4-(6-methoxypyridin-3-yl)phenyl]-2-[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]pentanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (63 mg) was added to a solution of the compound obtained from Example 1A above (100 mg), tri-n-butylphosphine (93 mg), and acetic acid (1 mL) in dry tetrahydrofuran (3 mL) at 0° C. The reaction mixture was stirred for 1 hour and concentrated. The residue was taken in ethyl acetate, and washed with water and brine. The organic layer was concentrated to get an oily residue which was purified on preparative thin layer chromatography (2 mm thickness) using 10% methanol in dichloromethane to get the title compound (80 mg).

Workup

  1. concentrationconcentrated
  2. washwashed with water and brine
  3. concentrationThe organic layer was concentrated
  4. customto get an oily residue which
  5. customwas purified on preparative thin layer chromatography (2 mm thickness)

Sources & evidence

ORD record
ord-e2d3d6e66be447498fdf0cd51cfe5a70
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Reaction notes

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