Triethylamine → HCID 86668863, compound

HRID 1507668Notes

Reaction equation

HRID 1507668 reaction equation
[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:15][CH2:14][C:13]([CH2:17]C(O)=O)([OH:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:23]([CH2:26]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1>C1(C)C=CC=CC=1.O1CCCC1>[O:35]=[C:26]1[NH:23][CH2:17][C:13]2([CH2:14][CH2:15][C@@H:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:12]2)[O:16]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67114044HCID 67114044, compound

Product 1

HCID 86668863HCID 86668863, compoundYield 15.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-((3R)-3-(benzyloxycarbonyl)-1-hydroxycyclopentyl)acetic acid (from step B, 130 mg, 0.467 mmol) in a mixture of toluene (2 mL) and tetrahydrofuran (1.0 mL) was added triethylamine (0.098 mL, 0.701 mmol) and diphenylphosphoryl azide (154 mg, 0.561 mmol) at room temperature. The resulting mixture was heated to 80° C. for 45 min. The reaction mixture was concentrated and the residue was subjected to preparative HPLC (Shimadzu VP-ODS 20×100 mm, 8 min. gradient, Solvent A: 10% MeOH, 90% H2O, 0.1% TFA; Solvent B: 90% MeOH, 10% H2O, 0.1% TFA). The fractions corresponding to the individual diasteromers were collected, concentrated, freeze dried and taken forward individually. Isomer 1: 20 mg, 0.073 mmol, 15.5% yield, MS (ESI+) m/z 276 (M+H)+; Isomer 2: 20 mg, 0.073 mmol, 15.5% yield, MS (ESI+) m/z 276 (M+H)+

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customwas subjected to preparative HPLC (Shimadzu VP-ODS 20×100 mm, 8 min. gradient, Solvent A: 10% MeOH, 90% H2O, 0.1% TFA; Solvent B: 90% MeOH, 10% H2O, 0.1% TFA)
  3. customThe fractions corresponding to the individual diasteromers were collected
  4. concentrationconcentrated
  5. customfreeze dried

Sources & evidence

ORD record
ord-c71944d971864e24942d201e787bba75
Source dataset
uspto-grants-2015_12
Patent number
US09221819B2

Reaction notes

Loading…