Trifluoroacetic acid → HCID 59750666, compound

HRID 422252Notes

Reaction equation

HRID 422252 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[N:14]([CH2:21][CH:22]1[C:31]2[C:26](=[C:27]([O:32][C:33]3[CH:38]=[CH:37][C:36]([C:39](=[O:41])[NH2:40])=[CH:35][N:34]=3)[CH:28]=[CH:29][CH:30]=2)[CH2:25][CH2:24][CH2:23]1)[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])(C)(C)C>C(Cl)Cl>[CH3:19][CH:18]([CH3:20])[CH2:17][CH2:16][CH2:15][NH:14][CH2:21][CH:22]1[CH2:23][CH2:24][CH2:25][C:26]2[C:27]([O:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]([NH2:40])=[O:41])=[CH:35][N:34]=3)=[CH:28][CH:29]=[CH:30][C:31]1=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66673819HCID 66673819, compound

Product 1

HCID 59750666HCID 59750666, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add TFA (540 mg, 4.73 mmol) to a solution of [5-(5-Carbamoyl-pyridin-2-yloxy)-1,2,3,4-tetrahydro-naphthalen-1-ylmethyl]-(4-methyl-pentyl)-carbamic acid tert-butyl ester (114 mg, 0.236 mmol) and DCM (3 ml) stirring under nitrogen at ambient temperature. After 18 hours, concentrate the mixture, redissolve in EtOAc and wash with 1M aq. K2CO3, water, and brine. Dry (MgSO4), concentrate, and purify on silica gel (5% (1N NH3/MeOH)/DCM) to obtain the title compound (80 mg) as an off-white solid. Mass spectrum (ion spray): m/z=382 (M+1); 1HNMR (CDCl3): 8.56 (s, 1H), 8.15 (d, 1H), 7.21-7.13 (m, 2H), 6.90 (m, 2H); 6.04 (br. s, 2H), 3.01 (m, 1H), 2.90-2.79 (m, 2H), 2.68-2.55 (m, 3H), 2.49-2.41 (m, 1H), 1.84-1.64 (m, 4H), 1.57-1.46 (m, 3H), 1.19 (m, 2H), 0.87 (d, 6H).

Workup

  1. concentrationconcentrate the mixture
  2. dissolutionredissolve in EtOAc
  3. washwash with 1M aq. K2CO3, water, and brine
  4. dry with materialDry (MgSO4)
  5. concentrationconcentrate
  6. custompurify on silica gel (5% (1N NH3/MeOH)/DCM)

Sources & evidence

ORD record
ord-efffa0125c764967aca5d535a8572e8a
Source dataset
uspto-grants-2012_01
Patent number
US08101638B2

Reaction notes

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