Tributylamine → Emtricitabine

HRID 404538Notes

Reaction equation

HRID 404538 reaction equation
C(N(CCCC)CCCC)CCC.[CH2:14]1[S:18][C@H:17]([CH2:19][OH:20])[O:16][C@@H:15]1[N:21]1[C:26](=[O:27])[N:25]=[C:24]([NH2:28])[C:23]([F:29])=[CH:22]1.Cl>ClCCl>[CH2:14]1[S:18][C@H:17]([CH2:19][OH:20])[O:16][C@@H:15]1[N:21]1[C:26](=[O:27])[N:25]=[C:24]([NH2:28])[C:23]([F:29])=[CH:22]1

Participants

4

Reactant 2

HCID 7622TributylamineHCID 53311196HCID 53311196, compound

Product 1

HCID 60877Emtricitabine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tri-n-butyl amine (76.76 g) was added to a solution of emtricitabine hydrochloride (101 g; Example 3) in dichloromethane (450 mL) in 30 minutes at 25° C. to 30° C. The solution was stirred at 25° C. to 30° C. for about 5 hours. The product was filtered, washed with dichloromethane (112.5 mL) and dried under vacuum at 40° C. to 45° C. for about 14 hours.

Workup

  1. filtrationThe product was filtered
  2. washwashed with dichloromethane (112.5 mL)
  3. customdried under vacuum at 40° C. to 45° C. for about 14 hours

Sources & evidence

ORD record
ord-e63f11ac20784170855bf445f6bd8b86
Source dataset
uspto-grants-2014_06
Patent number
US08748604B2

Reaction notes

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