Trifluoroacetic acid → HCID 86637855, compound

HRID 1518225Notes

Reaction equation

HRID 1518225 reaction equation
C(OC([N:8](C(OC(C)(C)C)=O)[CH:9]([C:38]([O:40][CH3:41])=[O:39])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=2)[C:13]([CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[C:12]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH:36]=[O:37])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH:9]([C:38]([O:40][CH3:41])=[O:39])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=2)[C:13]([CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]2)=[C:12]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH:36]=[O:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86637854methyl 1-{2-[bis(tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl}-3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylate

Product 1

HCID 86637855HCID 86637855, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 1-{2-[bis(tert-butoxycarbonyl)amino]-3-methoxy-3-oxopropyl}-3-cyclohexyl-2-(2-formylphenyl)-1H-indole-6-carboxylate in DCM (0.05 M) a large excess (>100 eq) of TFA was added and the solution stirred at RT for 20 min. Volatiles were removed in vacuo and the residue partitioned between EtOAc and aqueous NaHCO3. The organic phase was washed with brine before being dried over Na2SO4, filtered and the solvent evaporated in vacuo to afford the title compound (quant). MS (ES+) m/z 463 (M+H)+.

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue partitioned between EtOAc and aqueous NaHCO3
  3. washThe organic phase was washed with brine
  4. dry with materialbefore being dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-19a25f4826664969a84cefd000d23dca
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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