Trityl chloride → HCID 21886526, compound

HRID 2216095Notes

Reaction equation

HRID 2216095 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20].C(N(C(C)C)CC)(C)C.[C:30](Cl)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl>[C:30]([N:3]1[N:2]=[N:1][C:5]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[N:4]1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 81531DiisopropylethylamineHCID 21886449HCID 21886449, compound

Product 1

HCID 21886526HCID 21886526, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(2H-tetrazol-5-yl)-butyl]-isoindole-1,3-dione (4.07 g, 15.0 mmol) and diisopropylethylamine (7.8 mL, 45.0 mmol) in DCM (60 mL) was added trityl chloride (5.86 g, 21.0 mmol). The solution was stirred at ambient temperature for 14 h, and concentrated. The resulting residue was partitioned between EtOAc/DCM (3:1) and H2O. Organic layer was separated, washed with H2O and brine, dried over Na2SO4, concentrated, and flash chromatographed on silica gel, eluting with DCM/hexane (40, 80, and 100%) followed by EtOAc/DCM (1 and 2%) to give the title compound (5.08 g, 66% yield) as a pale yellow solid.

Workup

  1. concentrationconcentrated
  2. customThe resulting residue was partitioned between EtOAc/DCM (3:1) and H2O
  3. customOrganic layer was separated
  4. washwashed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customflash chromatographed on silica gel
  8. washeluting with DCM/hexane (40, 80, and 100%)

Sources & evidence

ORD record
ord-7633a4d16c1d42a980e69000b5c5c1b2
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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