Triethylamine → HCID 86699922, compound

HRID 530484Notes

Reaction equation

HRID 530484 reaction equation
O[C@H:2]([CH3:18])[C@H:3]([NH:7][C:8]([O:10][C:11]1([CH3:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:9])[C:4]([OH:6])=[O:5].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl>[CH3:17][C:11]1([O:10][C:8](=[O:9])[NH:7][C@H:3]2[C:4](=[O:6])[O:5][C@H:2]2[CH3:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724699PyBOPHCID 86699921HCID 86699921, compound

Product 1

HCID 86699922HCID 86699922, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a round bottomed flask equipped with a magnetic stirrer and a dropping funnel (2S,3R)-3-hydroxy-2-[(1-methylcyclohexoxy)carbonylamino]-butanoic acid (0.503 g, 1.95 mmol) was dissolved in anhydrous CH2Cl2 (50 mL). The clear yellow solution was cooled to 0° C., PyBOP (1.22 g, 2.34 mmol) was added, followed by a dropwise addition of Et3N solution (0.815 mL, 5.85 mmol) in anhydrous CH2Cl2 (5 mL), over a period of 10 min. The crude mixture was stirred at 0° C. for 1 h then overnight at rt. The reaction was quenched by addition of 5% NaHCO3 solution (50 mL) and the corresponding mixture was vigorously stirred for 10 min. The two phases were separated and the organic one collected, dried over Na2SO4 and concentrated to dryness to leave an oil, which was purified by typical chromatography eluting with petroleum ether/AcOEt mixtures (from 9:1 to 7:3). The title compound was obtained as white solid (0.070 g, 15%). m.p.: 92-93° C. MS (ESI) m/z: 242.2 [M−H]+; (ESI) m/z: 240.1 [M−H]−. 1H NMR (DMSO-d6): δ 1.15-1.60 (m, 8H) 1.35 (d, J=6.3 Hz, 3H), 1.42 (s, 3H), 2.02 (m, 2H), 4.83 (m, 1H), 5.35 (dd, J=9.2, 6.3 Hz, 1H), 7.98 (d, J=9.2 Hz, 1H).

Workup

  1. customovernight
  2. customat rt
  3. customThe reaction was quenched by addition of 5% NaHCO3 solution (50 mL)
  4. customThe two phases were separated
  5. customthe organic one collected
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customto leave an oil, which
  9. customwas purified by typical chromatography
  10. washeluting with petroleum ether/AcOEt mixtures (from 9:1 to 7:3)

Sources & evidence

ORD record
ord-e2aaaa70806748dd88bc439bc6099eaa
Source dataset
uspto-grants-2016_05
Patent number
US09353075B2

Reaction notes

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