Trifluoroacetic acid → HCID 18986934, compound

HRID 2397076Notes

Reaction equation

HRID 2397076 reaction equation
C([O:5][C:6]([NH:8][CH:9]([CH:22]1[C:34]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=1)=[O:11])=O)(C)(C)C.F[C:36](F)(F)C(O)=O>>[C:6]([NH:8][CH:9]([CH:22]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=2[C:29]2[C:34]1=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:10]([O:12][CH2:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=1)=[O:11])(=[O:5])[CH3:36]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18986945HCID 18986945, compound

Product 1

HCID 18986934HCID 18986934, compound

Procedure

3,5-Dimethylbenzyl N-t-butoxycarbonyl-2-(9-fluorenyl)glycinate (Example 9d, 0.5g) was dissolved in trifluoroacetic acid (10ml) for 40 minutes then evaporated in vacuo. To a solution of the residue in pyridine (10ml) was added acetic anhydride (1ml) for 16h. The solvent was removed in vacuo and the residue crystallised from diethyl ether/petroleum ether bp 60°-80° C. to give the title compound mp 162°-164° C. Found: C, 78.19; H,. 6.26; N, 3.45. C26H25NO3 requires C,. 78.17; H, 6.30; N, 3.50%. m/z (CI+)=400 (M+H), (CI-)=398 (M-H).

Workup

  1. customthen evaporated in vacuo
  2. additionTo a solution of the residue in pyridine (10ml) was added acetic anhydride (1ml) for 16h
  3. customThe solvent was removed in vacuo
  4. customthe residue crystallised from diethyl ether/petroleum ether bp 60°-80° C.

Sources & evidence

ORD record
ord-3041e64aa7a8491292bb2e3a728079e5
Source dataset
uspto-grants-1996_02
Patent number
US05495047

Reaction notes

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