Trifluoroacetic acid → 8-Amino-2E-octenoic acid trifluoroacetate salt

HRID 1534836Notes

Reaction equation

HRID 1534836 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C([NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])(OC(C)(C)C)=O>O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15679328N-Boc-8-amino-2E-octenoic acid

Product 1

HCID 867449568-Amino-2E-octenoic acid trifluoroacetate salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 45 mL trifluoroacetic acid and mL water was chilled in an ice bath while 34 g (0.132 mole) of (9) was added with stirring. The resulting solution was allowed to warm to room temperature over 1.5 h and then evaporated under a slow nitrogen stream overnight. The residue was triturated with ether. The solid was filtered, rinsed well with ether and dried to yield 21 g of the title compound (10), mp 77°-78° C. Anal. Calcd. for C10H15NO4F3 : C, 44.28; H, 5.95; N, 5.16. Found: C, 4.07; H, 5.96; N, 5.09.

Workup

  1. additionwas added
  2. customevaporated under a slow nitrogen
  3. customThe residue was triturated with ether
  4. filtrationThe solid was filtered
  5. washrinsed well with ether
  6. customdried

Sources & evidence

ORD record
ord-c7c62ff770f4474fb163e04108b62665
Source dataset
uspto-grants-1992_02
Patent number
US05091396

Reaction notes

Loading…