Trifluoroacetic acid → HCID 72713171, compound

HRID 1055469Notes

Reaction equation

HRID 1055469 reaction equation
C(O)(C(F)(F)F)=O.[C:8]([C:10]1[N:11]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[C:57]#[N:58])[C:12]2[C:17]([C:18]=1[CH2:19][N:20]1[C:31](=[O:32])[C@@H:30]([NH:33][C:34](=[O:46])[C@@H:35]([N:37](C)[C:38](=O)OC(C)(C)C)[CH3:36])[C:24]3([CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)[O:23][C:22]3[CH:47]=[CH:48][CH:49]=[CH:50][C:21]1=3)=[CH:16][CH:15]=[CH:14][CH:13]=2)#[N:9].C([O-])(O)=O.[Na+].O>C(Cl)Cl>[C:8]([C:10]1[N:11]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[C:57]#[N:58])[C:12]2[C:17]([C:18]=1[CH2:19][N:20]1[C:31](=[O:32])[C@@H:30]([NH:33][C:34](=[O:46])[C@@H:35]([NH:37][CH3:38])[CH3:36])[C:24]3([CH2:25][CH2:26][O:27][CH2:28][CH2:29]3)[O:23][C:22]3[CH:47]=[CH:48][CH:49]=[CH:50][C:21]1=3)=[CH:16][CH:15]=[CH:14][CH:13]=2)#[N:9]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 86585896Sodium bicarbonate waterHCID 131736367HCID 131736367, compound

Product 1

HCID 72713171HCID 72713171, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (37.0 g, 25 mL, 324 mmol, Eq: 55.9) was added dropwise over 2 h to a solution of tert-butyl (S)-1-((S)-5-((2-cyano-1-(2-cyanophenyl)-1H-indol-3-yl)methyl)-4-oxo-2′,3′,4,5,5′,6′-hexahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-3-ylamino)-1-oxopropan-2-yl(methyl)carbamate (4 g, 5.81 mmol) in DCM (50 mL) at 0° C. After 30 min. the mixture was added to sat. NaHCO3/H2O 1:1, the organic phase was separated, dried over Na2SO4, filtered and concentration to give the title compound (3.4 g, 97%) as a light yellow solid. MS m/z 589 (MH+)

Workup

  1. customthe organic phase was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentration

Sources & evidence

ORD record
ord-162aff8d198842f38f0171112ff93565
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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