Triethylamine → HCID 53323798, compound

HRID 2042950Notes

Reaction equation

HRID 2042950 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[C@@H:18]([OH:19])[C@H:17]([OH:20])[C@@H:16]([OH:21])[C@H:15]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([CH2:29][C:30]4[S:31][C:32]([C:35]5[O:36][CH:37]=[CH:38][CH:39]=5)=[CH:33][N:34]=4)[CH:23]=3)[O:14]2)(=O)=O)=CC=1.[NH:40]1[CH:44]=[N:43][N:42]=[N:41]1.C(N(CC)CC)C>CN(C=O)C>[N:40]1[N:41]([CH2:12][C@@H:13]2[C@@H:18]([OH:19])[C@H:17]([OH:20])[C@@H:16]([OH:21])[C@H:15]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([CH2:29][C:30]4[S:31][C:32]([C:35]5[O:36][CH:37]=[CH:38][CH:39]=5)=[CH:33][N:34]=4)[CH:23]=3)[O:14]2)[N:42]=[N:43][CH:44]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86680891HCID 86680891, compoundHCID 178418441HCID 178418441, compound

Product 1

HCID 53323798HCID 53323798, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The solution of toluenesulfonate 90 (612 mg, 1.03 mmol), tetrazole (0.45 M in acetonitrile) (11.5 mL 5.17 mmol) and triethyl amine (0.72 mL 5.17 mmol) in DMF (2.0 mL) was stirred at 80° C. for 3 d. Reaction mixture was evaporated under reduced pressure. The residue was purified by prep HPLC (C18) to afford the titled compound 98 (120 mg, 24%) as a solid.

Workup

  1. customReaction mixture
  2. customwas evaporated under reduced pressure
  3. customThe residue was purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-9dcaa6a6ce354d6caaff7d2f3591ad1e
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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