Trityl chloride → HCID 86681593, compound

HRID 1912366Notes

Reaction equation

HRID 1912366 reaction equation
[NH2:1][C@H:2]([C:18]([N:20]([O:22][CH3:23])[CH3:21])=[O:19])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:6][CH:5]=1.CCN(CC)CC.[C:31](Cl)([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CCOC(C)=O>C(Cl)Cl>[CH3:23][O:22][N:20]([CH3:21])[C:18](=[O:19])[C@@H:2]([NH:1][C:31]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86681594HCID 86681594, compound

Product 1

HCID 86681593HCID 86681593, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of amine 62 (0.38 g, 1.16 mmol) in DCM (15 mL) was added Et3N (1.2 eq., 1.40 mmol, 195 μL), and tritylchloride (1.2 eq., 1.40 mmol, 0.40 g) and the mixture was stirred for 14 hours. DCM was evaporated under reduced pressure and the residue was dissolved in EtOAc, extracted with 10 mM aq. HCl (2×) and brine, dried over MgSO4 and concentrated under reduced pressure. The title compound was obtained after column chromatography (10%->50% EtOAc/PE) as a colorless foam (yield: 0.61 g, 1.11 mmol, 96%). 1H NMR (400 MHz, CDCl3): δ=7.46 (s, 1H), 7.36 (d, J=7.55 Hz, 6H), 7.22-7.02 (m, 13H), 6.95 (s, 1H), 4.01-3.95 (m, 1H), 3.10 (s, 3H), 2.88 (dd, J=13.31, 5.95 Hz, 1H), 2.73 (dd, J=13.03, 7.26 Hz, 1H), 2.61 (s, 3H), 1.49 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3): δ=174.86, 152.68, 145.93, 136.93, 132.49, 130.36, 128.66, 127.31, 125.82, 118.18, 79.91, 70.58, 59.93, 41.63, 31.92, 28.15 ppm. [α]D23=+75.8 (c=1, CHCl3). HRMS: calcd. for C35H39N3O4 566.30133 [M+H]+. found 566.30120.

Workup

  1. customDCM was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. extractionextracted with 10 mM aq. HCl (2×) and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2db8f2ef41f74ecd88d9b8b7c74fc371
Source dataset
uspto-grants-2013_12
Patent number
US08609610B2

Reaction notes

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