Trifluoroacetic acid → HCID 58551277, compound

HRID 2204145Notes

Reaction equation

HRID 2204145 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:32]=[CH:31][C:9]2[N:10]3[C:28]([C:29]#[N:30])=[CH:27][CH:26]=[C:11]3[C:12]3([CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[O:13][C:8]=2[CH:7]=1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6]1[CH:32]=[CH:31][C:9]2[N:10]3[C:28]([C:29]#[N:30])=[CH:27][CH:26]=[C:11]3[C:12]3([CH2:14][CH2:15][NH:16][CH2:17][CH2:18]3)[O:13][C:8]=2[CH:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67469186HCID 67469186, compound

Product 1

HCID 58551277HCID 58551277, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 7′-(acetoxymethyl)-1′-cyano-spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-1-carboxylate was dissolved in CH2Cl2 (10 mL) before TFA (5.0 mL, 65 mmol) was added. The solvent was removed under reduced pressure to give (1′-cyanospiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-7′-yl)methyl acetate (15 mg, 62%). ESI-MS m/z calc. 337.1, found 338.3 (M+1)+; Retention time 1.16 minutes (3 min run).

Workup

  1. additionwas added
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3de923fe0fd54750a135e357d09c3cc1
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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