Trifluoroacetic acid → HCID 86590986, compound

HRID 982661Notes

Reaction equation

HRID 982661 reaction equation
C([O:5][C:6]([C@H:8]([N:10]1[C:15](=[O:16])[C@@H:14]([N:17]=[N+:18]=[N-:19])[C@@H:13]([OH:20])[CH2:12][O:11]1)[CH3:9])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:6]([C@H:8]([N:10]1[C:15](=[O:16])[C@@H:14]([N:17]=[N+:18]=[N-:19])[C@@H:13]([OH:20])[CH2:12][O:11]1)[CH3:9])([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86590987HCID 86590987, compound

Product 1

HCID 86590986HCID 86590986, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0˜−5° C.) stirred solution of the tert-butyl ester 11 (0.469 g, 1.64 mmol) in CH2Cl2 (8 ml), a precooled (ca. 0° C.) trifluoroacetic acid (6.5 mL) was added portionwise. The reaction mixture was kept for 1.5 hours at room temperature and was evaporated in vacuo to dryness. Traces of trifluoroacetic acid were removed by repeated addition and evaporation of dry ether (3×15 mL). After drying in vacuo, 0.373 g (99%) of the product 12 was obtained as a yellowish semisolid. 1H NMR (400 MHz) in CDCl3 (J, Hz): δ 1.58 (3H, d, 3J=7.4, α-MeCH), 4.10-4.06 (1H, m, 5-H), 4.13 (1H, dd, 2J=−11.7, 3J=4.1 , 6-HA), 4.31 (1H, dd, 2J=−11.7, 3J=5.9, 6-HB), 4.43 (1H, d, 3J=7.4, 4-H), H), 5.12 (1H, q, 3J=7.4, α-CH), 6.51 (2H, br. s, OH, COOH). 13C (100 MHz) in CD3CN: δ 13.51, 54.74, 65.75, 71.38, 78.21, 167.55, 170.91. IR (film), cm−1: 3456, 2959, 2125, 1746, 1654, 1284. MS (CI, isobutane), m/Z: 231 (M++1). The compound was used in the next reaction without further purification.

Workup

  1. temperatureTo a cooled (0˜−5° C.)
  2. customwas evaporated in vacuo to dryness
  3. customTraces of trifluoroacetic acid were removed
  4. additionaddition and evaporation of dry ether (3×15 mL)
  5. customAfter drying in vacuo

Sources & evidence

ORD record
ord-6a100a3bc71b45c4806db81934bfef62
Source dataset
uspto-grants-2005_03
Patent number
US06861416B2

Reaction notes

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