Triethylamine → HCID 69733389, compound

HRID 584781Notes

Reaction equation

HRID 584781 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C@@H:6]1[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@H:9]([O:20][C:21](=[O:23])[CH3:22])[CH2:8][NH:7]1.CCN(CC)CC.[C:31](Cl)([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>ClCCl>[CH2:34]([O:33][C:31]([N:7]1[CH2:8][C@@H:9]([O:20][C:21](=[O:23])[CH3:22])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)=[O:32])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 69733325HCID 69733325, compound

Product 1

HCID 69733389HCID 69733389, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of the product of Example 37 (189 mg, 0.58 mmol) in dichloromethane (2.5 mL) was added Et3N (0.10 mL, 0.72 mmol), and the mixture was cooled to 0° C. CbzCl (0.11 mL, 0.73 mmol) was added dropwise, and the solution was warmed up room temperature for 2 h. The reaction was quenched with aqueous NaCl, extracted with dichloromethane several times. The combined organic layer was dried over MgSO4. After the removal of volatiles, the residue was chromatographed on silica gel using hexanes-EtOAc (3:1) and hexanes-EtOAc (1:1) to yield pure product (138 mg) and starting material (5.81) (75 mg), 86% yield based on the consumed (5.81). Contain two rotamers at rt. 1H NMR (360 MHz, MeOD-d4) δ 7.55-7.48 (m, 1H), 7.38-7.21 (m, 5H), 6.50-6.33 (m, 2H), 5.90 (d, J2,3=5.7 Hz, 0.5H, H2), 5.87 (d, J2,3=5.7 Hz, 0.5H, H2), 5.76 (t, J4,3=J4,5=9.6 Hz, 0.5H, H4), 5.74 (t, J4,3=J4,5=9.6 Hz, 0.5H, H4), 4.99 (ddd, J5,6b=10.9 Hz, J5,4=9.6 Hz, J5,6a=5.6 Hz, H5), 4.39 (dd, J6a,6b=13.0 Hz, J6a,5=5.6 Hz, 0.5H, H6a), 4.35 (dd, J6a,6b=13.0 Hz, J6a,5=5.6 Hz, 0.5H, H6a), 3.07 (dd, J6b,6a=13.0 Hz, J6b,5=10.9 Hz, 0.5H, H6b) 2.97 (dd, J6b,6a=13.0 Hz, J6b,5=10.9 Hz, 0.5H, H6b), 2.00 (s, 3H), 1.99 (s, 3H), 1.87 (s, 3H).

Workup

  1. temperaturethe solution was warmed up room temperature for 2 h
  2. customThe reaction was quenched with aqueous NaCl
  3. extractionextracted with dichloromethane several times
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. customAfter the removal of volatiles
  6. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-e1d2b87997854f81a4ec378c1bb2b016
Source dataset
uspto-grants-2005_08
Patent number
US06927294B1

Reaction notes

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